Sodium Hydroxide → HCID 59800133, compound

HRID 1037578Notes

Reaction equation

HRID 1037578 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:18]([O:20]CC)=[O:19])=[CH:13][CH:12]=3)[CH:6]=[CH:5][N:4]=1.[OH-].[Na+:24]>C(O)C>[Na+:24].[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:18]([O-:20])=[O:19])=[CH:13][CH:12]=3)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59800135Ethyl 2-[2-(methylamino)pyrimidin-4-yl]-1H-indole-5-carboxylate

Product 1

HCID 59800133HCID 59800133, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25 g of ethyl 2-(2-methylaminopyrimidin-4-yl)-1H-indole-5-carboxylate were admixed with 200 ml of ethanol and 24.5 g of 33% sodium hydroxide solution, and heated to from 65° C. to 70° C. for 4 h. After cooling, the mixture was filtered with suction and the precipitate was washed with 15 ml of ethanol/water (9:1). 24.5 g (87.6% of theory) of 2-(2-methylaminopyrimidin-4-yl)-1H-indole-5-carboxylic acid sodium salt were obtained (98.1 HPLC area %). LCMS: [M+H]⊕ 269.10

Workup

  1. temperatureheated to from 65° C. to 70° C. for 4 h
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered with suction
  4. washthe precipitate was washed with 15 ml of ethanol/water (9:1)

Sources & evidence

ORD record
ord-fc540dc49b2b432db08a248bf1c48d95
Source dataset
uspto-grants-2013_10
Patent number
US08546567B2

Reaction notes

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