Water → HCID 20395302, compound

HRID 261206Notes

Reaction equation

HRID 261206 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][CH:7]3[CH:11]([C:12](=[O:13])[C:4]=2[CH:3]=1)[CH2:10][N:9]([CH3:14])[CH2:8]3.[CH3:17][Li].[Cl-].[NH4+].O>O1CCCC1.CCOCC>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][CH:7]3[CH:11]([C:12]([CH3:17])([OH:13])[C:4]=2[CH:3]=1)[CH2:10][N:9]([CH3:14])[CH2:8]3

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 20395303HCID 20395303, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 20395302HCID 20395302, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 43 g of 6-chloro-3a,4,9,9a-tetrahydro-2-methylbenz[f]isoindolin-4-one in 430 ml of tetrahydrofuran is added dropwise at room temperature with stirring to 170 ml of a ca. 5% solution of methyl lithium in ether in a nitrogen atmosphere and the mixture is stirred for 51/2 hours at room temperature. Thereafter, saturated ammonium chloride solution and water are added and the mixture extracted with methylene chloride. The organic phase is dried over sodium sulphate and evaporated. The residue is crystallised from ether/petroleum ether to yield 6-chloro-3a,4,9,9a-tetrahydro-2,4-dimethylbenz[f]-isoindolin-4-ol. M.P. 125°-130°.

Workup

  1. extractionthe mixture extracted with methylene chloride
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. customevaporated
  4. customThe residue is crystallised from ether/petroleum ether

Sources & evidence

ORD record
ord-0e0ac72ebbb948ba90562eab13197d52
Source dataset
uspto-grants-1979_08
Patent number
US04164583

Reaction notes

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