Acetate → Pigment Yellow 213

HRID 1415915Notes

Reaction equation

Cl.[NH2:2][C:3]1[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].N([O-])=O.[Na+].[C:21]([O-:24])(=O)[CH3:22].C([N:31]1[C:40]2[C:35](=[CH:36][C:37]([O:42][CH3:43])=[C:38]([NH2:41])[CH:39]=2)[NH:34][C:33](=[O:44])[C:32]1=[O:45])(=O)CC(C)=O>>[O:24]=[C:21]([CH3:22])[CH:38]([C:37](=[O:42])[NH:41][C:38]1[CH:39]=[C:40]2[C:35]([NH:34][C:33](=[O:44])[C:32](=[O:45])[NH:31]2)=[CH:36][C:37]=1[O:42][CH3:43])[N:41]=[N:2][C:3]1[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

Reactant 4

HCID 175Acetate

HCID 22600739HCID 22600739, compound

HCID 22600740HCID 22600740, compound

HCID 23668193Sodium Nitrite

Product 1

HCID 11113951Pigment Yellow 213

Conditions

Temperature: 96 °C

Procedure

0.1 mol of dimethyl aminoterephthalate hydrochloride is diazotized with sodium nitrite at from 0 to 10° C. The clarified diazonium salt solution is added dropwise at room temperature over 1 hour to an acetate-buffered suspension of 0.1 mol of N-acetoacetyl-6-methoxy-7-aminoquinoxaline-2,3-dione in the presence of a sufactant, such as ®LUTENSOL AT 25. When coupling is at an end the mixture is heated to 96° C.and the product is filtered and washed free of salt. The moist presscake is suspended in N-methylpyrrolidone, the water is removed by distillation and the product is subsequently heated at from 100 to 170° C. It is then cooled to 70° C., filtered, dried and milled. This gives 51 g of a yellow pigment.

Workup

filtrationand the product is filtered
washwashed free of salt
customthe water is removed by distillation
temperaturethe product is subsequently heated at from 100 to 170° C
temperatureIt is then cooled to 70° C.
filtrationfiltered
customdried
custommilled

Sources & evidence

ORD record: ord-2a260704320f4e45b2dbae23a8c9cf4e
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05910577

Reaction notes

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