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

HRID 461502Notes

Reaction equation

HRID 461502 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, diluted 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-7797c1349b64444fbb7425dbf8db686c
Source dataset
uspto-grants-1977_12
Patent number
US04062961

Reaction notes

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