Ammonia → 6-chloro-5,7-dimethyl-4-oxo-4H-1-benzopyran-2-carboxamide

HRID 1580696Notes

Reaction equation

HRID 1580696 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:16]=[C:15]([CH3:17])[C:14]([Cl:18])=[C:13]([CH3:19])[C:9]=2[C:10](=[O:12])[CH:11]=1)=O)C.[NH3:20]>C(O)C>[Cl:18][C:14]1[C:15]([CH3:17])=[CH:16][C:8]2[O:7][C:6]([C:4]([NH2:20])=[O:3])=[CH:11][C:10](=[O:12])[C:9]=2[C:13]=1[CH3:19]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 540826896-chloro-5,7-dimethyl-4-oxo-4H-1-benzopyran-2-carboxylic acid ethyl ester

Product 1

HCID 213925996-chloro-5,7-dimethyl-4-oxo-4H-1-benzopyran-2-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 50.1 parts of 6-chloro-5,7-dimethyl-4-oxo-4H-1-benzopyran-2-carboxylic acid ethyl ester in 750 parts of warm ethanol was saturated with dry ammonia. After 2 hours a solid had precipitated out and the slurry was heated on the steam bath to remove excess ammonia. The solid was filtered off and crystallised from dimethylformamide to give 42.3 parts of 6-chloro-5,7-dimethyl-4-oxo-4H-1-benzopyran-2-carboxamide, melting point >300°C.

Workup

  1. customAfter 2 hours a solid had precipitated out
  2. temperaturethe slurry was heated on the steam bath
  3. customto remove excess ammonia
  4. filtrationThe solid was filtered off
  5. customcrystallised from dimethylformamide

Sources & evidence

ORD record
ord-531a6702120c40fda47f9e77d93ed089
Source dataset
uspto-grants-1976_01
Patent number
US03933844

Reaction notes

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