Hydrochloric Acid → HCID 19972449, compound

HRID 1452274Notes

Reaction equation

C([C:3]1[C:12]2[O:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:9]([CH3:19])[C:8](=[O:20])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=O.[C:21](O)(=O)[CH2:22][C:23]([OH:25])=[O:24].N1CCCCC1.Cl>N1C=CC=CC=1>[C:23](/[CH:22]=[CH:21]/[C:3]1[C:12]2[O:11][C:10]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[C:9]([CH3:19])[C:8](=[O:20])[C:7]=2[CH:6]=[CH:5][CH:4]=1)([OH:25])=[O:24]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7.92 g of 8-formyl-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran (prepared as described in Uneyama, K. et al., Bull. Chem. Soc. Jap. 58.; 2361, (1985)) 3.75 g of malonic acid and 0.46 ml of piperidine in 15 ml of anhydrous pyridine was stirred at 100° C. for 3 hours. After cooling to 20°-25° C. the reaction mixture was poured into a mixture of 90 g of crushed ice and 33 ml of hydrochloric acid (d=1.18). The resultant precipitate was collected by suction filtration, washed with water and crystallized twice from 95% ethanol to give 5.5 g of the title compound, m.p. 226°-229° C.

Workup

temperatureAfter cooling to 20°-25° C. the reaction mixture
filtrationThe resultant precipitate was collected by suction filtration
washwashed with water
customcrystallized twice from 95% ethanol

Sources & evidence

ORD record: ord-c95f0f58920c4301a2c4e74ceec8141f
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05605896

Reaction notes

Loading…