N-Hydroxy-1,1,1-trimethylsilanamine → HCID 54681154, compound

HRID 2294205Notes

Reaction equation

HRID 2294205 reaction equation
C[Si]([NH:5][OH:6])(C)C.[OH:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=2)[NH:11][C:10](=[O:21])[C:9]=1[C:22](OCC)=[O:23]>O1CCOCC1>[OH:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=2)[NH:11][C:10](=[O:21])[C:9]=1[C:22]([NH:5][OH:6])=[O:23]

Participants

4

Reactant 2

HCID 21936899N-Hydroxy-1,1,1-trimethylsilanamineHCID 54681153Ethyl 4-hydroxy-7-nitro-2-oxo-1,2-dihydro-quinoline-3-carboxylate

Product 1

HCID 54681154HCID 54681154, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

4 ml of trimethylsilylhydroxylamine (30 mmol) were sprayed at room temperature into a suspension of 1.38 g of ethyl 4-hydroxy-7-nitro-2-oxo-1,2-dihydro-quinoline-3 -carboxylate (5 mmol) in 40 ml of dioxan. After heating to 100° C. all passed slowly into solution. The reaction mixture was left to stir at 90° C. for 20 hrs., cooled to room temperature and the separated voluminous precipitate was filtered off. This was washed with water and dried in a high vacuum. 740 mg of 4,N-dihydroxy-7-nitro-2-oxo-1,2-dihydro-quinoline-3-carboxamide (65%) were obtained as pale beige crystals.

Workup

  1. waitThe reaction mixture was left
  2. temperature, cooled to room temperature
  3. filtrationthe separated voluminous precipitate was filtered off
  4. washThis was washed with water
  5. customdried in a high vacuum

Sources & evidence

ORD record
ord-d54afb4fa48e4259a4db5f9bca58e54b
Source dataset
uspto-grants-1997_11
Patent number
US05688803

Reaction notes

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