Ethyl 2-(3-chloroisoquinolin-1-yl)acetate → 2-(3-Chloro-isoquinolin-1-yl)acetamide

HRID 506882Notes

Reaction equation

C([O:3][C:4](=O)[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([Cl:16])[N:7]=1)C.[NH3:18].CO>>[Cl:16][C:8]1[N:7]=[C:6]([CH2:5][C:4]([NH2:18])=[O:3])[C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

Reactant 2

HCID 11379685Ethyl 2-(3-chloroisoquinolin-1-yl)acetate

HCID 21705897Ammonia methanol

Product 1

HCID 187708522-(3-Chloro-isoquinolin-1-yl)acetamide

Procedure

(3-chloro-isoquinolin-1-yl)-acetic acid ethyl ester (2.5 g, 10 mmol) is dissolved in 4N NH3/MeOH (50 ml). The solution is transferred into an autoclave and kept at 120° C. for 48 hours. After cooling to RT the solvent is removed and the resulting crude product is purified on silica gel using methylene chloride (100%)→methylene chloride/methanol (95/5) as eluent, affording 2-(3-chloro-isoquinolin-1-yl)-acetamide as a pale yellow solid.

Workup

customis removed
customthe resulting crude product is purified on silica gel

Sources & evidence

ORD record: ord-fa456336eee64405afaa5fed78be5aec
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786123B2

Reaction notes

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