Methanol → HCID 23062593, compound

HRID 491838Notes

Reaction equation

HRID 491838 reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[C:8]([C:11]([O:13]C)=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1)=[O:16].CO.[OH-].[Na+]>O1CCCC1>[NH2:1][C:2]1[C:6]2[CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1)=[O:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 23062579HCID 23062579, compound

Product 1

HCID 23062593HCID 23062593, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-5-methoxycarbonyl-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (2.01 g) is suspended in tetrahydrofuran (20 ml)-methanol, thereto is added 4 N aqueous sodium hydroxide solution (5 ml) under ice-cooling and the reaction solution is stirred at room temperature for 13 hours. The reaction solution is concentrated under reduced pressure, the resulting residue is diluted with water, and the mixture is adjusted to around pH 3 by pouring 10% hydrochloric acid. The precipitates are collected by filtration, washed with water and ethanol successively and dried to give the title compound (1.87 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution is concentrated under reduced pressure
  3. additionthe resulting residue is diluted with water
  4. additionby pouring 10% hydrochloric acid
  5. filtrationThe precipitates are collected by filtration
  6. washwashed with water and ethanol successively
  7. customdried

Sources & evidence

ORD record
ord-559d8bb0048f4821a24e9d0d45015609
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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