2-Naphthalenol, 1-amino-1,2,3,4-tetrahydro- synthesis

5synthesis methods

Product Name:2-Naphthalenol, 1-amino-1,2,3,4-tetrahydro-
CAS Number:90874-85-4
Molecular formula:C10H13NO
Molecular Weight:163.22

2-Naphthalenol, 1-bromo-1,2,3,4-tetrahydro-

1195628-70-6
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2-Naphthalenol, 1-amino-1,2,3,4-tetrahydro-

90874-85-4
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Yield:90874-85-4 76%

Reaction Conditions:

with ammonium hydroxide in methanol;water at 20;

Steps:

1-amino-1,2,3,4-tetrahydronaphthalen-2-ol (106)

Compound 105 (770 mg, 3.4 mmol) was dissolved in 2 mL of meOH after which aqueous ammonium hydroxide (4 mL, 29 mmol) was added. The mixture was stirred overnight at ambient temperature. TLC verified disappearance of the starting product and the meOH was evaporated. The residue was purified directly by silica gel chromatography (gradient system 0 to 10% meOH/100 to 90% ch₂Cl₂). Product 106 was obtained in the form of a white solid (423 mg, 76%). R (aE 100): 0.19. ¹H NMR (400 MHz, dMSO-d₆) δ 7.52 (m, 1H), 7.24 (m, 2H), 7.16 (m, 1H), 5.46 (br s, 1H, OH), 4.02 (m, 1H), 3.80 (m, 1H), 2.81 (m, 2H), 2.02 (m, 1H), 1.75 (m, 1H). ¹³C NMR (101 MHz, dMSO-d₆) δ 136.6, 132.9, 128.7, 128.0, 127.7, 126.1, 68.5, 55.3, 28.2, 26.3. IR (diamond aTR, cm^-1) ν 2929, 1598, 1493, 1043, 774, 742, 552. HRMS (EI-MS): m/z calculated for C₁₀H₁₄NO [M+H]⁺: 164.1069, found: 164.1070. T_m: 155-160° C.