p-Toluenesulfonic acid → HCID 66816010, compound

HRID 1697105Notes

Reaction equation

HRID 1697105 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])[CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20](=O)[CH2:21][CH2:22][C:23](=O)[CH3:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:18][C:16]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([NH:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([N:1]3[C:23]([CH3:24])=[CH:22][CH:21]=[C:20]3[CH3:19])[N:7]=2)[CH:17]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80352,5-HexanedioneHCID 66817303HCID 66817303, compound

Product 1

HCID 66816010HCID 66816010, compoundYield 77.1%

Procedure

A slurry of 2-(6-amino-pyridin-2-ylamino)-4-chlorobenzoic acid (2.4 g) and 2,5-hexanedione (1.04 g) and p-toluenesulfonic acid (0.15 g) was heated at reflux in a Dean-Stark trap for 24 h. The resulting mixture was cooled to RT and filtered, then stirred with H2O (50 mL) overnight, filtered, and dried to yield 4-chloro-2-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-ylamino]-benzoic acid (2.4 g).

Workup

  1. temperatureat reflux in a Dean-Stark trap for 24 h
  2. filtrationfiltered
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-cb468fec63c8475eb4f3c0a33ae0a607
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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