Methanol → (S)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

HRID 1161268Notes

Reaction equation

HRID 1161268 reaction equation
[Cl:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[CH:6]=[CH:5]2.Cl.[NH2:17][C@@H:18]([CH3:22])[C:19]([NH2:21])=[O:20].C(N(CC)CC)C.CO>>[Cl:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:17]([C@@H:18]([CH3:22])[C:19]([NH2:21])=[O:20])[CH:6]=[CH:5]2

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 2775816(S)-2-aminopropanamide hydrochlorideHCID 595157256-Chloro-5-nitro-1H-isochromen-1-one

Product 1

HCID 59515834(S)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

Conditions

Temperature
60 °C

Procedure

A mixture of 6-chloro-5-nitro-1H-isochromen-1-one (230 mg, 0.00102 mol), (S)-2-aminopropanamide hydrochloride (127 mg, 0.00102 mol), triethylamine (142 μL, 0.00102 mol) and methanol (20 mL, 0.5 mol) was stirred at 60° C. for 3 hours. The solvent was removed and the residue purified by flash chromatography to obtain the product as a yellow solid. MS m/z=262.3 (M+H).

Workup

  1. customThe solvent was removed
  2. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-eed38aa5b79e446ab8d22d7845f3016c
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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