5-Chloro-2-methoxybenzoyl chloride → 3-(5-Chloro-2-methoxybenzamido)-2,2-dimethyl-7-methoxy-4-chromanone

HRID 1457757Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].Cl.[NH2:14][CH:15]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][C:20]([O:26][CH3:27])=[CH:21][CH:22]=2)[O:17][C:16]1([CH3:29])[CH3:28]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([NH:14][CH:15]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][C:20]([O:26][CH3:27])=[CH:21][CH:22]=2)[O:17][C:16]1([CH3:29])[CH3:28])=[O:8]

Participants

Conditions

Temperature: 27 °C

Procedure

28.7 g (0.14 mol) of 5-chloro-2-methoxybenzoyl chloride were introduced into a solution of 33.5 g (0.13 mol) of 3-amino-2,2-dimethyl-7-methoxy-4-chromanone hydrochloride in 150 ml of pyridine at 10° C. After the mixture had been stirred at about 27° C. for three hours, it was introduced into ice/water and extracted twice with methylene chloride. The combined methylene chloride extracts were washed twice with 2N hydrochloric acid and with water and then dried and evaporated, and the residue was recrystallized from ethanol/DMF. The 3-(5-chloro-2-methoxybenzamido)-2,2-dimethyl-7-methoxy-4-chromanone had a melting point of 174° C.

Workup

extractionextracted twice with methylene chloride
washThe combined methylene chloride extracts were washed twice with 2N hydrochloric acid and with water
customdried
customevaporated
customthe residue was recrystallized from ethanol/DMF

Sources & evidence

ORD record: ord-f677be56fc5548a49005494e33cd7261
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849755

Reaction notes

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