Sodium Hydroxide → 2-Benzyl-2,3-dihydro-1H-isoindole-4-carboxylic acid

HRID 1494849Notes

Reaction equation

HRID 1494849 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:17]([O:19]C)=[O:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O>[CH2:1]([N:8]1[CH2:16][C:15]2[C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19828480Methyl 2-benzylisoindoline-4-carboxylate

Product 1

HCID 221368252-Benzyl-2,3-dihydro-1H-isoindole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

48 1 g of 2-benzyl-4-methoxycarbonylisoindoline prepared in Reference Example 14-(3) was added to a solution of 16 g of sodium hydroxide in 160 ml of water and the mixture was heated under reflux for 3 hours. After removing insoluble materials by filtration, the filtrate was adjusted to pH 5 with 6 N hydrochloric acid. The resulting crystals were collected by filtration, and was washed with water, cold ethanol, ether, and then chloroform to give 35.0 g of 2-benzylisoindoline-4-carboxylic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customAfter removing insoluble materials
  4. filtrationby filtration
  5. filtrationThe resulting crystals were collected by filtration
  6. washwas washed with water, cold ethanol, ether

Sources & evidence

ORD record
ord-bd6a5e26985c46f39da27d11871cc126
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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