Citric Acid → HCID 58306987, compound

HRID 1909890Notes

Reaction equation

HRID 1909890 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[C:20]([O:22]C)=[O:21])[CH:13]=[CH:12]1.CO.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:31]>C1COCC1>[OH:31][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH:3][C:2](=[O:1])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[C:20]([OH:22])=[O:21])[CH:13]=[CH:12]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 58306920HCID 58306920, compound

Product 1

HCID 58306987HCID 58306987, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To methyl 1-(1,3-benzoxazol-2-ylmethyl)-1H-indole-7-carboxylate (0.22 g), methanol (2.0 mL), and THF (2.0 mL) was added a 1 M aqueous sodium hydroxide solution (1.0 mL), followed by stirring at 70° C. for 14 hours. The reaction mixture was ice-cooled, a 10% aqueous citric acid solution (5.0 mL) was added thereto, and the precipitated solid was collected by filtration, and washed with water and diethyl ether/hexane (1/1) to obtain 1-{2-[(2-hydroxyphenyl)amino]-2-oxo ethyl}-1H-indole-7-carboxylic acid (0.18 g).

Workup

  1. temperaturecooled
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water and diethyl ether/hexane (1/1)

Sources & evidence

ORD record
ord-91bf63c92cd749d7b7fe2a2aa7a3aaf4
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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