Sodium Bicarbonate → HCID 9801448, compound

HRID 257773Notes

Reaction equation

HRID 257773 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:31])[N:9]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH:23]=[C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)[C:10](=[O:14])[NH:11]2)=[CH:6][CH:5]=1)([O-])=[O:2].C(=O)(O)[O-].[Na+]>C(O)C>[OH:2][NH:1][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:31])[N:9]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:20][CH:21]=[C:22]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:23][CH2:24]3)[C:10](=[O:14])[NH:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 19092317HCID 19092317, compound

Product 1

HCID 9801448HCID 9801448, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 7-nitro-3-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]-1,2,3,4-tetrahydroquinazoline-2,4-dione (0.2 g) in ethanol (10 ml) was added. Stannous chloride (0.46 g) and the mixture was refluxed for 30 minutes. After cooling, an aqueous sodium bicarbonate was added to adjust the pH to 7 and inorganic salts were filtered off through filter cell. The filter cake was washed with hot ethanol. Combined filtrate and washings were evaporated and the crude residue was washed in turn with water and cold ethanol, and then dried to give crystals of 7-hydroxyamino-3-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]-1,2,3,4-tetrahydroquinazoline-2,4-dione (85 mg).

Workup

  1. temperatureAfter cooling
  2. filtrationwere filtered off
  3. filtrationthrough filter cell
  4. washThe filter cake was washed with hot ethanol
  5. customCombined filtrate and washings were evaporated
  6. washthe crude residue was washed in turn with water and cold ethanol
  7. customdried

Sources & evidence

ORD record
ord-ef43424c73a04b989de20c2a64599943
Source dataset
uspto-grants-1993_11
Patent number
US05264438

Reaction notes

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