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

HRID 1288478Notes

Reaction equation

HRID 1288478 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.N>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 222AmmoniaHCID 7918Acetic AnhydrideHCID 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

7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.001 mole) was treated with sodium acetate (0.001 mole), acetic anhydride (0.00125 mole), and 2 ml. of acetic acid and the mixture was heated at 95° C. for 15 minutes. The mixture was cooled, dilutes with water, made alkaline with aqueous ammonia and extracted with chloroform. Concentration of the extract and recrystallization of the residue from isopropanol gave 2-acetyl-7,8-dichloro-1,2,3,4-tetrahydroisoquinoline, m.p. 99.5°-100° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with chloroform
  3. extractionConcentration of the extract
  4. customrecrystallization of the residue from isopropanol

Sources & evidence

ORD record
ord-9ed9f44bb4904e11bf51b742a59aff85
Source dataset
uspto-grants-1976_10
Patent number
US03988339

Reaction notes

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