Water → 2-(2-Methylanilino)-benzene-1,4-dicarboxylic acid

HRID 2418481Notes

Reaction equation

HRID 2418481 reaction equation
Br[C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:14][C:15]1[C:16]([CH3:21])=[CH:17][CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+].O>C(OCCO)C>[CH3:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:14][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7242O-ToluidineHCID 11430Potassium CarbonateHCID 68513Bromoterephthalic acid

Product 1

HCID 204464572-(2-Methylanilino)-benzene-1,4-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
150 °C

Procedure

Bromoterephthalic acid (12.2 g), ortho-toluidine (10.7 ml), anhydrous K2CO3 (13.8 g), catalytic Cu powder (0.2 g) in 2-ethoxy-ethanol (17.5 ml) were stirred together while heating under reflux conditions in an oil bath at 150° C. After 6 hours, water (200 ml) was added and, when all salts had dissolved, the solution was clarified and crude product precipitated by acidification to pH 2. The collected diacid was well washed with boiling water then recrystallised from 50% ethanol, pure product being obtained as yellow needles of mp 318° C. (dec).

Workup

  1. dissolutionwhen all salts had dissolved
  2. customcrude product precipitated by acidification to pH 2
  3. washThe collected diacid was well washed with boiling water
  4. customthen recrystallised from 50% ethanol, pure product
  5. custombeing obtained as yellow needles of mp 318° C. (dec)

Sources & evidence

ORD record
ord-783e3e59088348b2abf579d757a85da6
Source dataset
uspto-grants-1984_09
Patent number
US04472582

Reaction notes

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