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Water → 6-(4-Hydroxypiperidino)-5-nitro-3,4 dihydrocarbostyril

HRID 487350
Notes
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Reaction equation

HRID 487350 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]3)[CH2:4][CH2:3]1.[N:19]([O-:21])=[O:20].[Na+].O.CO.C(Cl)(Cl)Cl>C(O)(=O)C>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][C:17]=2[N+:19]([O-:21])=[O:20])[NH:14][C:13](=[O:18])[CH2:12][CH2:11]3)[CH2:4][CH2:3]1.[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([N+:19]([O-:21])=[O:20])=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]3)[CH2:4][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 190947066-(4-Hydroxypiperidino)-3,4-dihydrocarbostyrilHCID 21584188Chloroform methanolHCID 23668193Sodium Nitrite

Product 2

HCID 190946986-(4-Hydroxypiperidino)-5-nitro-3,4 dihydrocarbostyrilHCID 190947006-(4-Hydroxypiperidino) 7-nitro-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3.1 g of 6-(4-hydroxypiperidino)-3,4-dihydrocarbostyril in 60 ml of acetic acid was added 1.7 g of sodium nitrite. After stirring at room temperature for 1 hr, water and a 17% methanol-chloroform mixture was added to the reaction mixture. The organic layer was washed with water, dried, and evaporated under a reduced pressure. The crude mixture was purified by a silica gel column chromatography and recrystallized from 2-propanol to give 1.1 g of 6-(4-hydroxypiperidino) 7-nitro-3,4-dihydrocarbostyril and 130 mg of 6-(4-hydroxypiperidino)-5-nitro-3,4 dihydrocarbostyril.

Workup

  1. washThe organic layer was washed with water
  2. customdried
  3. customevaporated under a reduced pressure
  4. customThe crude mixture was purified by a silica gel column chromatography
  5. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-c8a2ba29fded4107a4a94ae3236fffde
Source dataset
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05294718

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes