Sodium Hydroxide → HCID 20196475, compound

HRID 652739Notes

Reaction equation

HRID 652739 reaction equation
[C:1]([NH:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([CH3:28])=[CH:13][N:14]3[C:21](=[O:22])[C:20]([C:23]([O:25]CC)=[O:24])=[CH:19][N:18]=[C:15]32)=[CH:10][CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+]>CO>[C:1]([NH:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([CH3:28])=[CH:13][N:14]3[C:21](=[O:22])[C:20]([C:23]([OH:25])=[O:24])=[CH:19][N:18]=[C:15]32)=[CH:10][CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20196469HCID 20196469, compound

Product 1

HCID 20196475HCID 20196475, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of ethyl 10-pivaloylamino-7-methyl-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (400 mg) and 1N sodium hydroxide (3.1 ml) in aqueous methanol (19 ml) was stirred at ambient temperature for 2 days. Aqueous methanol was added to the reaction mixture and then heated on a water bath until almost all the precipitate was dissolved. The solution was filtered, and the filtrate was acidified with 1N hydrochloric acid. The resultant precipitate was collected, washed successively with water and methanol, and dried. Recrystallization from a mixture of N,N-dimethylformamide and water gave pure 10-pivaloylamino-7-methyl-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylic acid (0.31 g).

Workup

  1. temperatureheated on a water bath until almost all the precipitate
  2. dissolutionwas dissolved
  3. filtrationThe solution was filtered
  4. customThe resultant precipitate was collected
  5. washwashed successively with water and methanol
  6. customdried
  7. customRecrystallization
  8. additionfrom a mixture of N,N-dimethylformamide and water

Sources & evidence

ORD record
ord-27e4bb4cc4ad46a081d3cbed4dc95af7
Source dataset
uspto-grants-1987_06
Patent number
US04673676

Reaction notes

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