Acetic Anhydride → HCID 12838038, compound

HRID 327402Notes

Reaction equation

HRID 327402 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][NH:10][CH2:9][CH2:8]2.[OH-].[Na+].C([O-])(O)=O.[Na+].[C:20](OC(=O)C)(=[O:22])[CH3:21]>ClCCl>[C:20]([N:10]1[CH2:9][CH2:8][C:7]2[C:12](=[C:3]([Cl:2])[CH:4]=[CH:5][CH:6]=2)[CH2:11]1)(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 125950728-Chloro-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

Product 1

HCID 12838038HCID 12838038, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 28.6 g of 8-chloro-1,2,3,4-tetrahydoisoquinoline hydrochloride in 140 ml of dichloromethane was added 140 ml of 1N aqueous NaOH solution and 17.6 g of NaHCO3. To the solution was added dropwise 14.5 ml of acetic anhydride at 5° C. The mixture was stirred at room temperature for 1 hour. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with water, dried over anhydrous sodium sulfate. The solvent was distilled off to give 29.1 g of the title compound as a pale red oil.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-95ad5da48c2b4f3eac985c169b57df40
Source dataset
uspto-grants-1993_12
Patent number
US05273974

Reaction notes

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