Water → HCID 19842260, compound

HRID 280544Notes

Reaction equation

HRID 280544 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:23])[C:11]2[C:12](=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)[C:13](N)=[O:14])=[CH:5][CH:4]=1.[BH4-].[Na+].O>CO.O1CCCC1>[OH:14][CH:13]1[C:12]2[C:11](=[CH:19][CH:18]=[C:17]([N+:20]([O-:22])=[O:21])[CH:16]=2)[C:10](=[O:23])[N:9]1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19842265HCID 19842265, compound

Product 1

HCID 19842260HCID 19842260, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(4-methoxyphenyl)-4-nitrophthalamide (12 g) was suspended in a mixture of methanol (80 ml) and tetrahydrofuran (80 ml) and, under ice-cooling and stirring, sodium borohydride (1.6 g) was added. Water (300 ml) was added to the mixture and crude crystals were collected by filtration to give a mixture (11 g) of 3-hydroxy-2-(4-methoxyphenyl)-5-nitroisoindolin-1-one and 3-hydroxy-2-(4-methoxyphenyl)-6-nitroisoindolin-1-one. The mixture (6.0 g) thus obtained and piperidinocarbonylmethylenetriphenylphosphoran (9.3 g) were dissolved in toluene (200 ml) under heating, and the solution was refluxed for 3 hours. After cooling, crystals separated were collected by filtration and recrystallized from toluene to give 2.2 g of 2-(4-methoxyphenyl)-6-nitro-3-piperidinocarbonylmethylisoindolin-1-one.

Workup

  1. temperaturecooling
  2. filtrationcrude crystals were collected by filtration

Sources & evidence

ORD record
ord-0bec638b0a6647fca78f6878e89ccda5
Source dataset
uspto-grants-1986_05
Patent number
US04590189

Reaction notes

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