C.I. Basic Red 9 monohydrochloride → HCID 86742952, compound

HRID 621404Notes

Reaction equation

HRID 621404 reaction equation
[N+]([O-])([O-])=O.[Na+].[CH:6]1[C:12](=[C:13]([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH:11]=[CH:10][C:8](=[NH:9])[CH:7]=1.Cl.[CH:29]1C(C(C2C=CC(N)=CC=2)=C2C=CC(=N)C=C2)=CC=C(N)C=1.[N+]([O-])([O-])=O.[OH-:55].[Na+]>NC1C=CC=CC=1>[CH:6]1[C:12]([C:13]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)=[C:21]2[CH:22]=[CH:23][C:24](=[NH:27])[CH:25]=[CH:26]2)=[CH:11][CH:10]=[C:8]([NH2:9])[CH:7]=1.[CH3:29][OH:55]

Participants

6

Reactant 4

HCID 11292C.I. Basic Red 9 monohydrochlorideHCID 14798Sodium HydroxideHCID 24268Sodium NitrateHCID 86742953HCID 86742953, compound

Product 1

HCID 86742952HCID 86742952, compound

Reagents, catalysts & solvents 1

HCID 6115AnilineSolvent

Procedure

From an alkali blue process stream is isolated 274 g of crude pararosaniline nitrate, formed by adding concentrated aqueous sodium nitrate to the pararosaniline hydrochloride reaction mixture. The pararosaniline nitrate is dissolved in 650 g aniline at 80° C. to which 54 g of 50 percent aqueous sodium hydroxide is slowly added to bring the pH to 11.5 to 12.5. The aqueous layer is allowed to separate, is drawn off, and the organic layer allowed to cool. Crystals of pararosaniline carbinol base are isolated as a filter cake weighing 151 g and assaying 62 percent by weight pararosaniline carbinol. Following toluene wash to remove residual aniline, the dry, slightly pink carbinol base assays at 98 percent purity.

Workup

  1. customformed
  2. additionis slowly added
  3. customto separate
  4. temperatureto cool

Sources & evidence

ORD record
ord-be5fad68322e460090e8edb0d4649697
Source dataset
uspto-grants-1989_04
Patent number
US04824610

Reaction notes

Loading…