Dichloromethane methanol acetic acid water → 2-(4'Carboxyphenylazo)-6 acetyl morphine

HRID 461761Notes

Reaction equation

HRID 461761 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][CH:12]2[C:25](C(=O)C)([OH:26])[C:24]3[O:30][C@@H:21]4[C@@:22]56[CH2:31][CH2:32][N:33]([CH3:34])[C@@H:16]([C@@H:17]5[CH:18]=[CH:19][C@:20]4([C:36](=[O:38])[CH3:37])[OH:35])[CH2:15][C:14]([C:23]6=3)=[CH:13]2)=[CH:6][CH:5]=1)([OH:3])=[O:2].C(Cl)Cl.CO.O.C(O)(=O)C>[OH-].[Na+]>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12]2[C:25]([OH:26])=[C:24]3[O:30][C@@H:21]4[C@@:22]56[CH2:31][CH2:32][N:33]([CH3:34])[C@@H:16]([C@@H:17]5[CH:18]=[CH:19][C@:20]4([C:36](=[O:38])[CH3:37])[OH:35])[CH2:15][C:14](=[C:23]63)[CH:13]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 18914200Dichloromethane methanol acetic acid waterHCID 867352922-(4'Carboxyphenylazo)-3,6-diacetylmorphine

Product 1

HCID 1364097552-(4'Carboxyphenylazo)-6 acetyl morphine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.5g of 2-(4'carboxyphenylazo)-3,6-diacetylmorphine in 10 ml 0.1 N NaOH was stirred at room temperature and examined hourly by silica gel TLC for the presence of the monoacetyl derivative, the solvent system being methylene chloride: methanol: water: acetic acid (80:20:1:1) and the rf value for azomonoacetyl morphine 0.39. When TLC showed most of the starting material to have hydrolyzed the reaction mixture was concentrated and passed down a silica gel column. The fraction containing the desired product was evaporated to dryness to give 2-(4'carboxyphenylazo) -6 acetyl morphine.

Workup

  1. concentrationwas concentrated
  2. additionThe fraction containing the desired product
  3. customwas evaporated to dryness

Sources & evidence

ORD record
ord-d59f681817c547c0beba15d2d5cc8863
Source dataset
uspto-grants-1977_12
Patent number
US04064228

Reaction notes

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