Acetic Anhydride → HCID 13051705, compound

HRID 127915Notes

Reaction equation

HRID 127915 reaction equation
Cl.[CH2:2]([S:9][C:10]1[C:19]([N+:20]([O-:22])=[O:21])=[C:18]2[C:13]([CH2:14][CH2:15][NH:16][CH2:17]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].C([O-])(=O)C.[Na+]>C(O)(=O)C>[C:23]([N:16]1[CH2:15][CH2:14][C:13]2[C:18](=[C:19]([N+:20]([O-:22])=[O:21])[C:10]([S:9][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:11][CH:12]=2)[CH2:17]1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 20523212HCID 20523212, compound

Product 1

HCID 13051705HCID 13051705, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 17.5 g. (0.052 mole) of 7-benzylthio-8-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride, 15 ml. of acetic anhydride and 4.5 g. (0.055 mole) of sodium acetate in 150 ml. of acetic acid was heated on a steam bath for one hour, then evaporated. Water and aqueous ammonia was added to the residue until the mixture was basic. The mixture was extracted with methylene chloride, the extracts combined and washed with water, 10% hydrochloric acid, 5% sodium bicarbonate, dried over sodium sulfate and concentrated. Chromatography of the residue on silica (ethyl acetate) gave 2-acetyl-7-benzylthio-8-nitro-1,2,3,4-tetrahydroisoquinoline, melting point 94°-95° C.

Workup

  1. additionA mixture of 17.5 g
  2. customevaporated
  3. additionWater and aqueous ammonia was added to the residue until the mixture
  4. extractionThe mixture was extracted with methylene chloride
  5. washwashed with water, 10% hydrochloric acid, 5% sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-61efef1f251c46c3b68e1701f806fe7f
Source dataset
uspto-grants-1981_03
Patent number
US04258049

Reaction notes

Loading…