Hydrochloric Acid → HCID 14075008, compound

HRID 2291820Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[CH:13]=[CH:14][CH:15]=[C:16]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[C:21]([OH:28])[C:20]=3[CH2:29][CH2:30][CH3:31])[C:9]2=[N:8][CH:7]=1)=[O:5])C.Cl>C(O)(=O)C>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][C:16]2[C:9]3=[N:8][CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:11](=[O:12])[N:10]3[CH:13]=[CH:14][CH:15]=2)=[C:20]([CH2:29][CH2:30][CH3:31])[C:21]=1[OH:28])(=[O:27])[CH3:26]

Participants

Conditions

Temperature: 80 °C

Procedure

0.90 g (2.12 mmoles) of 9-(4-acetyl-3-hydroxy-2-n-propylphenoxymethyl)-4-oxo-pyrido[1,2-a]pyrimidine-3carboxylic acid ethyl ester and 8 ml of 6N hydrochloric acid were added to 36 ml of acetic acid, and this mixture was heated at 80° C. for 8 hours with stirring. After cooling, the resulting reaction solution was concentrated under reduced pressure, followed by the addition of an appropriate amount of water. The solid matter which separated out was collected by filtration and washed with water. This precipitate was dried and then recrystallized from a mixture of tetrahydrofuran and methanol to obtain 0.42 g (50% yield) of 9-(4-acetyl-3-hydroxy-2-n-propylphenoxymethyl)-4-oxo-pyrido[1,2-a]-pyrimidine-3-carboxylic acid in the form of white crystals. These crystals had a melting point of 170°-172° C.

Workup

temperatureAfter cooling
customthe resulting reaction solution
concentrationwas concentrated under reduced pressure
additionfollowed by the addition of an appropriate amount of water
customThe solid matter which separated out
filtrationwas collected by filtration
washwashed with water
customThis precipitate was dried
customrecrystallized from a mixture of tetrahydrofuran and methanol

Sources & evidence

ORD record: ord-930b8a41ffe94e7b8316de162b510be9
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04798832

Reaction notes

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