Hydrochloric Acid → (E)-4-[3-Oxo-3-[1,2,3,4-tetrahydro-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one-2-yl]-1-propenyl]benzoic acid

HRID 988316Notes

Reaction equation

HRID 988316 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12](=[O:36])[N:13]2[CH2:25][C:24]3[C:23](=[O:26])[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[NH:16][C:15]=3[CH:14]2[C:27]2[CH:32]=[CH:31][C:30]3[O:33][CH2:34][O:35][C:29]=3[CH:28]=2)=[CH:6][CH:5]=1.[OH-].[Na+].Cl>CO>[O:36]=[C:12]([N:13]1[CH2:25][C:24]2[C:23](=[O:26])[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[NH:16][C:15]=2[CH:14]1[C:27]1[CH:32]=[CH:31][C:30]2[O:33][CH2:34][O:35][C:29]=2[CH:28]=1)/[CH:11]=[CH:10]/[C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:37])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12993029(E)-4-[3-Oxo-3-[1,2,3,4-tetrahydro-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one-2-yl]-1-propenyl]benzoic acid methyl ester

Product 1

HCID 12993031(E)-4-[3-Oxo-3-[1,2,3,4-tetrahydro-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one-2-yl]-1-propenyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-4-[3-oxo-3-[1,2,3,4-tetrahydro-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one-2-yl]-1-propenyl]benzoic acid methyl ester (149 mg, 0.30 mmol), (prepared as in Example 30) was suspended in a 1:1 mixture of 1N aqueous sodium hydroxide:methanol (10 mL) and heated to reflux for 8 h. The reaction mixture was treated with aqueous HCl to pH 1, resulting in a white precipitate. The precipitate was collected by filtration and washed with water (30 mL) and diethyl ether (160 mL) to yield the product as a white solid.

Workup

  1. temperatureto reflux for 8 h
  2. customresulting in a white precipitate
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water (30 mL) and diethyl ether (160 mL)

Sources & evidence

ORD record
ord-ba02810e19b34be782079253812c58b3
Source dataset
uspto-grants-2003_10
Patent number
US06635638B2

Reaction notes

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