Hydrochloric Acid → 3-(5-Chloro-2-methoxybenzamido)-2,2-dimethyl-7-methoxy-4-chromanol

HRID 1457758Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([CH:25]=1)[C:7]([NH:9][CH:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[CH:16][CH:17]=2)[O:12][C:11]1([CH3:24])[CH3:23])=[O:8].[BH4-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([CH:25]=1)[C:7]([NH:9][CH:10]1[CH:19]([OH:20])[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[CH:16][CH:17]=2)[O:12][C:11]1([CH3:23])[CH3:24])=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 25 g (64 mmol) of 3-(5-chloro-2-methoxybenzamido)-2,2-dimethyl-7-methoxy-4-chromanone and 1.24 g (32 mmol) of powdered sodium borohydride in 100 ml of ethanol was stirred at 50° C. for 3 hours, during which the solid dissolved. After cooling, the solution was then poured into ice-water acidified with hydrochloric acid, and extracted with methylene chloride. The organic solution was washed with water, dried and evaporated. The resulting 3-(5-chloro-2-methoxybenzamido)-2,2-dimethyl-7-methoxy-4-chromanol (diastereomer mixture) melted from 165° C.

Workup

dissolutiondissolved
temperatureAfter cooling
extractionextracted with methylene chloride
washThe organic solution was washed with water
customdried
customevaporated
custommelted from 165° C.

Sources & evidence

ORD record: ord-93ac96a592bd4a3caa9fe006c6ec8ddc
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849755

Reaction notes

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