3-HYDRAZINO-BENZOIC ACID ETHYL ESTER synthesis
- Product Name:3-HYDRAZINO-BENZOIC ACID ETHYL ESTER
- CAS Number:90556-87-9
- Molecular formula:C9H12N2O2
- Molecular Weight:180.2
582-33-2
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Yield:90556-87-9 91.7%
Reaction Conditions:
Stage #1: 3-aminobenzoic acid ethyl esterwith hydrogenchloride;NaNO2 in water monomer; for 0.5 h;Cooling with ice;
Stage #2: with hydrogenchloride;stannous chloride monohydrate in water monomer at 0; for 2 h;
Steps:
46.1 Step 1:
NaNO2 (1.52 g, 22.0 mmol) in H2O (10 mL) was added over 10 min to an ice-cooled and stirred suspension of ethyl 3-aminobenzoate (3.30 g, 20.0 mmol) in 6N HCl (30 mL). After an additional 30 min, a suspension of SnCl2·H2O (9.0 g, 40.0 mmol) in 6N HCl (30 mL) was added slowly and the resulting suspension was stirred at 0 °C for 2h. The pH was adjusted to 9-10 by 30% NaOH solution and the mixture was extracted with EtOAc (2 × 300 mL). The mixture was filtered and the solid was dried under reduced pressure to give the ethyl- 3-hydrazinobenzoate product (3.30 g, yield 91.7%) as a yellow solid. 1HNMR (400 MHz, DMSO-d6): δ 10.30 (s, 2H), 7.58-7.50 (m, 2H), 7.43 (t, J = 7.8 Hz, 1H), 7.22 (d, J = 7.6 Hz, 1H), 4.30 (q, J = 14.2, 7.1 Hz, 2H), 1.31 (t, J = 7.1 Hz, 3H) ppm.
References:
WO2022/40157,2022,A1 Location in patent:Paragraph 00396-00399
