HCID 54037887, compound → HCID 22612299, compound

HRID 844016Notes

Reaction equation

HRID 844016 reaction equation
C([O:3][C:4](=[O:29])[C:5]1[CH:6]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26](=[O:28])[NH2:27])[CH:21]=2)[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[CH:8]=[CH:9][CH:10]=1)C>C(O)C.[OH-].[Na+]>[C:26]([C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[O:19][CH:6]1[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[CH:8]=[CH:9][CH:10]=[C:5]1[C:4]([OH:29])=[O:3])(=[O:28])[NH2:27]

Participants

4

Reactant 1

HCID 54037887HCID 54037887, compound

Product 1

HCID 22612299HCID 22612299, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-(3-Carbamoyl-phenoxy)-N-(2-chloro-benzyl)-nicotinic acid ethyl ester (4.31 grams, 16.08 mmole) in ethanol (100 ml) and 1 N sodium hydroxide (40.21 ml) was refluxed for 4 hours. The mixture was concentrated to 1/3 volume, diluted to 300 ml with water, acidified to pH 3 with 1 N hydrochloric acid and filtered to isolate a white solid which was recrystalized from ethyl acetate/hexane (3.8 g). M.P. 220-224° C.; Anal. calcd. for C13H10N2O4: C, 60.45; H, 3.91; N, 10.85. Found: C, 61.70; H, 3.61; N, 10.69.

Workup

  1. concentrationThe mixture was concentrated to 1/3 volume
  2. additiondiluted to 300 ml with water
  3. filtrationfiltered
  4. customto isolate a white solid which
  5. customwas recrystalized from ethyl acetate/hexane (3.8 g)

Sources & evidence

ORD record
ord-6cb86866aeae44dd987c3874877c0b4a
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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