Water → HCID 54681152, compound

HRID 2294206Notes

Reaction equation

HRID 2294206 reaction equation
C[Si]([NH:5][OH:6])(C)C.[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:24])=[C:13]([C:19](OCC)=[O:20])[C:14](=[O:18])[NH:15]2)=[CH:10][CH:9]=1.O>CN(C)C=O>[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:24])=[C:13]([C:19]([NH:5][OH:6])=[O:20])[C:14](=[O:18])[NH:15]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21936899N-Hydroxy-1,1,1-trimethylsilanamineHCID 54695868HCID 54695868, compound

Product 1

HCID 54681152HCID 54681152, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2 ml of trimethylsilylhydroxylamine (15 mmol) were sprayed at room temperature into a suspension of 2.64 g of ethyl 7-chloro-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxylate (10 mmol) in 2.0 ml of dimethylformamide. After heating to 100° C. all passed slowly into solution. The reaction mixture was left to stir at 80° C. for 2 hrs., cooled to room temperature and stirred overnight. After the addition of 6 ml of water a voluminous precipitate separated and was filtered off, washed with water and dried in a high vacuum. 1.48 g of 7-chloro-4,N-dihydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxamide (58%) were obtained as pale beige crystals.

Workup

  1. waitThe reaction mixture was left
  2. temperature, cooled to room temperature
  3. stirringstirred overnight
  4. customseparated
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried in a high vacuum

Sources & evidence

ORD record
ord-659e8baeccf14b3a8199ddb78a532f86
Source dataset
uspto-grants-1997_11
Patent number
US05688803

Reaction notes

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