Acetic Anhydride → 1-(7,8-Dichloro-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

HRID 903565Notes

Reaction equation

HRID 903565 reaction equation
Cl.[Cl:2][C:3]1[C:12]([Cl:13])=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][CH2:10]2)=[CH:5][CH:4]=1.[C:14]([O-])(=[O:16])[CH3:15].[Na+].C(OC(=O)C)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)(=O)C>[C:14]([N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:12]([Cl:13])[C:3]([Cl:2])=[CH:4][CH:5]=2)[CH2:10]1)(=[O:16])[CH3:15]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 1239197,8-Dichloro-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)HCID 517045Sodium Acetate

Product 1

HCID 125951001-(7,8-Dichloro-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture containing (100 g., 0.425 m.) 7,8-dichlorotetrahydroisoquinoline hydrochloride and (41 g., 0.5 m.) sodium acetate in 760 ml. of acetic acid and 430 ml. of acetic anhydride was heated at 100° C. with stirring for four hours. The cooled reaction mixture was diluted with 800 ml. of water and brought to pH 8 by addition of 5% aqueous sodium carbonate (1400 ml.). The tan precipitate was collected by filtration, dried and recrystallized from isopropanol to give N-acetyl-7,8-dichloro-1,2,3,4-tetrahydroisoquinoline having a melting point of 98°-100° C.

Workup

  1. customThe cooled reaction mixture
  2. additionwas diluted with 800 ml
  3. filtrationThe tan precipitate was collected by filtration
  4. customdried
  5. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-8eb7cadf36944b41bbbdbb44d4b8e71b
Source dataset
uspto-grants-1980_10
Patent number
US04228170

Reaction notes

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