Chloroacetamide → carbamoylmethyl alpha,2-dimethyl-5H-[1]benzopyrano [2,3-b]pyridine-7-acetate

HRID 1382757Notes

Reaction equation

[CH3:1][CH:2]([C:6]1[CH:7]=[CH:8][C:9]2[O:19][C:13]3=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=[C:12]3[CH2:11][C:10]=2[CH:20]=1)[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]([NH2:31])=[O:30]>CN(C)C=O>[CH3:1][CH:2]([C:6]1[CH:7]=[CH:8][C:9]2[O:19][C:13]3=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=[C:12]3[CH2:11][C:10]=2[CH:20]=1)[C:3]([O:5][CH2:28][C:29](=[O:30])[NH2:31])=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2.7 g of α,2-dimethyl-5H-[1]benzopyrano [2,3-b]pyridine-7-acetic acid in 15 ml of dimethylformamide are added 0.8 g of potassium carbonate and 1.1 g of 2-chloroacetamide, and stirred at 80° C. for 1 hour under a nitrogen atmosphere. The reaction mixture is poured into ice water, and the precipitated crystals are collected by filtration, washed with water, and then recrystallized from ethanol to obtain 2.7 g of carbamoylmethyl α,2-dimethyl-5H-[1]benzopyrano [2,3-b]pyridine-7-acetate as white crystals having a melting point of 175° to 177° C.

Workup

filtrationthe precipitated crystals are collected by filtration
washwashed with water
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-0d9a1cda40a84146b64b574dcd2c4f40
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04808593

Reaction notes

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