1,2,3,4-Tetrahydro-8,9-dimethoxy-3-(2-morpholinoethyl)5H-[1]benzopyrano-[3,4-c]pyridin-5-one → 1,2,3,4-tetrahydro-8,9-dihydroxy-3-(2-morpholinoethyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one

HRID 267963Notes

Reaction equation

HRID 267963 reaction equation
C[O:2][C:3]1[C:8]([O:9]C)=[CH:7][C:6]2[C:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH2:13][C:12]=3[C:25](=[O:27])[O:26][C:5]=2[CH:4]=1>Br>[OH:2][C:3]1[C:8]([OH:9])=[CH:7][C:6]2[C:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)[CH2:13][C:12]=3[C:25](=[O:27])[O:26][C:5]=2[CH:4]=1

Participants

3

Reactant 1

HCID 214471711,2,3,4-Tetrahydro-8,9-dimethoxy-3-(2-morpholinoethyl)5H-[1]benzopyrano-[3,4-c]pyridin-5-one

Product 1

HCID 214471671,2,3,4-tetrahydro-8,9-dihydroxy-3-(2-morpholinoethyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 8.7 g 0f 1,2,3,4-tetrahydro-8,9-dimethoxy-3-(2-morpholinoethyl)-5H[1]benzopyrano[3,4-c]pyridin-5-one in 60 cc of 48% HBr was refluxed for 17 hr then cooled. Crystallization of precipitate from water afforded 5.5 g of product; mp 299°-302° C.

Workup

  1. temperaturethen cooled
  2. customCrystallization of precipitate from water

Sources & evidence

ORD record
ord-16d6a8a631394acabc0ade0fa10464a9
Source dataset
uspto-grants-1976_03
Patent number
US03946008

Reaction notes

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