Methanol → 1-(4-Amino-phenylazo)-4-(dimethylamino)naphtalene

HRID 28319

Reaction equation

HRID 28319 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([N:22]([CH3:24])[CH3:23])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.O.O.O.O.O.O.O.O.O.S([O-])(O)(=O)=O.[Na+].CO>O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([N:22]([CH3:24])[CH3:23])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3682098N,N-dimethyl-4-(4-nitrophenylazo)-1-naphthylamineHCID 131727008HCID 131727008, compound

Product 1

HCID 178385861-(4-Amino-phenylazo)-4-(dimethylamino)naphtalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15 g of 1-(4-nitro-phenylazo)-4-(dimethylamino)naphtalene, 75 ml sodiumhydrogen sulphate nonahydrate (50% wt in water) and 80 ml of methanol was heated at reflux for 3 h. The reaction mixture was then cooled to room temperature and poured into 300 ml of water. The brownish precipitate was filtered off, washed with water (200 ml) and cold methanol-water (100 ml/100 ml) to give 12 g of nearly pure 1-(4-amino-phenylazo)-4-(dimethylamino)naphtalene as a brownish solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. filtrationThe brownish precipitate was filtered off
  4. washwashed with water (200 ml) and cold methanol-water (100 ml/100 ml)

Sources & evidence

ORD record
ord-c8f077f3186244cda816f1911099ee60
Source dataset
uspto-grants-2008_09
Patent number
US07419620B2

Linked notes

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