Ethyl 2-amino-2-(5-bromo-3-chloropyridin-2-yl)acetate → (5-Bromo-3-chloropyridin-2-yl)methanamine hydrochloride

HRID 1503723Notes

Reaction equation

HRID 1503723 reaction equation
[NH2:1][CH:2]([C:8]1[C:13]([Cl:14])=[CH:12][C:11]([Br:15])=[CH:10][N:9]=1)C(OCC)=O>Cl>[ClH:14].[Br:15][C:11]1[CH:12]=[C:13]([Cl:14])[C:8]([CH2:2][NH2:1])=[N:9][CH:10]=1

Participants

3

Reactant 1

HCID 71138503Ethyl 2-amino-2-(5-bromo-3-chloropyridin-2-yl)acetate

Product 1

HCID 71138342(5-Bromo-3-chloropyridin-2-yl)methanamine hydrochlorideYield 182.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of ethyl 2-amino-2-(5-bromo-3-chloropyridin-2-yl)acetate (0.5 g, 1.7 mmol) in 3 N HCl (25 mL) was heated at reflux for 4 h. The reaction mixture was washed with diethyl ether and H2O. The combined ether layer was concentrated under reduced pressure to afford the title compound as an off-white solid (400 mg, 65%): 1H NMR (400 MHz, CDCl3) δ 8.78 (s, 1H), 8.70 (br s, 2H), 8.45 (s, 1H), 4.56 (m, 2H); ESIMS m/z 221.15 ([M+H]+).

Workup

  1. temperatureat reflux for 4 h
  2. washThe reaction mixture was washed with diethyl ether and H2O
  3. concentrationThe combined ether layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f91e6964fac7424486542fb38a19f3c7
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

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