Potassium Carbonate → 2-carbamoylethyl alpha,2-dimethyl-5H-[1]benzopyrano[2,3-b]pyridine7-acetate

HRID 1382758Notes

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][CH2:29][C:30]([NH2:32])=[O:31]>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][CH2:29][C:30](=[O:31])[NH2:32])=[O:4]

Participants

Conditions

Temperature: 70 °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 1.3 g of 3-chloropropionamide, and stirred at 70° C. for 7.5 hours under a nitrogen atmosphere. The reaction mixture is poured into ice water. The precipitate is extracted with ethyl acetate, washed with water and dried, and then concentrated. The residue is recrystallized from ethanol to obtain 2.4 g of 2-carbamoylethyl α,2-dimethyl-5H-[1]benzopyrano[2,3-b]pyridine7-acetate as white crystals having a melting point of 143° to 145° C.

Workup

extractionThe precipitate is extracted with ethyl acetate
washwashed with water
customdried
concentrationconcentrated
customThe residue is recrystallized from ethanol

Sources & evidence

ORD record: ord-af576c056a4f4b5e9b8c91f5fb1e8cc3
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04808593

Reaction notes

Loading…