ChemicalBook CAS DataBase List 2-BENZYLOXYANILINE

2-BENZYLOXYANILINE synthesis

10synthesis methods

Product Name:2-BENZYLOXYANILINE
CAS Number:20012-63-9
Molecular formula:C13H13NO
Molecular Weight:199.25

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20012-63-9
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Yield:20012-63-9 100%

Reaction Conditions:

with sodium hydroxide;sodium tetrahydridoborate;nickel (II) chloride in hydrogenchloride;methanol;

Steps:

55 3-amino-4-[1-[4-[N'-(2-hydroxyphenyl)ureido]-3-methoxyphenylacetamido]-2-pyrrolidinyl methoxy]benzoic Acid

To a stirred solution of 2-benzyloxynitrobenzene (9.92 g, 43.3 mmol) and NiCl₂ (20.3 g, 157 mmol) in MeOH (350 mL) was added portionwise NaBH₄ (8.09 g, 214 mmol) at 0° C. After disappearing of the starting material (monitored by TLC), the mixture was evaporated off. The black precipitate was dissolved in 1N HCl, then acidic solution was alkalified by the addition of 1N NaOH and extracted with EtOAc. The extracts were washed brine, dried over Na₂SO₄, and concentrated to dryness. Chromatography of the residue with CHCl₃ as eluent gave 2-benzyloxy aniline (8.60 g, 100%) as a reddish oil. ¹H-NMR (CDCl₃) δ 3.71 (broad s,2H), 5.06 (s, 2H), 6.68-6.86 (m, 4H), 7.32-7.44 (m, 5H); FAB-MS m/z 200 (M⁺+1).

References:

US2003/78249,2003,A1