Hydrochloric Acid → 3-(N-methylamino)aniline-4-sulfonic acid
Reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:11]=1[S:12]([OH:15])(=[O:14])=[O:13])[NH2:8])(=O)C.[OH-].[Na+].S(OC)(OC)(=O)=O.Cl.[Cl-].[Na+]>O.C(O)=O>[CH3:1][NH:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:11]=1[S:12]([OH:15])(=[O:14])=[O:13])[NH2:8]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
115 g of 3-(N-acetylamino)aniline-4-sulfonic acid in 430 ml of water and 70 g of formic acid were boiled under reflux for 7 hours. The mixture was cooled to 20° C. and its pH then adjusted to 12 with caustic soda solution. 75 g of dimethyl sulfate were then added, and after 40 minutes the pH was adjusted to -0.5 with hydrochloric acid. The mixture was heated under reflux for 3 hours and then salted out with 150 g of sodium chloride. The pH was adjusted to 1.0 with caustic soda solution, and the precipitated 3-(N-methylamino)aniline-4-sulfonic acid was isolated by filtration.
Workup
- temperatureunder reflux for 7 hours
- temperatureThe mixture was heated
- temperatureunder reflux for 3 hours
Sources & evidence
- ORD record
- ord-c5ed07ea8d9946d18376aabbd64f628d
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05117050
Reaction notes
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