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Sodium Bicarbonate → HCID 178433805, compound

HRID 384296
Notes
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Reaction equation

HRID 384296 reaction equation
[NH2:1][C:2]1[C:3]([OH:18])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[N:19]([O-])=O.[Na+].[CH2:23]1[C:31]2[C:26](=[CH:27][C:28]([N:32]3[C:36](=[O:37])[CH2:35][C:34]([CH3:38])=[N:33]3)=[CH:29][CH:30]=2)[CH2:25][CH2:24]1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[F:8][C:6]1[CH:7]=[C:2]([NH:1][N:19]=[C:35]2[C:36](=[O:37])[N:32]([C:28]3[CH:27]=[C:26]4[C:31](=[CH:30][CH:29]=3)[CH2:23][CH2:24][CH2:25]4)[N:33]=[C:34]2[CH3:38])[C:3]([OH:18])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=2)[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 210723153'-Amino-5'-fluoro-2'-hydroxy-biphenyl-3-carboxylic acidHCID 23668193Sodium NitriteHCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one

Product 1

HCID 178433805HCID 178433805, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent
HCID 702EthanolSolvent

Procedure

Upon cooling by an ice-water bath, 3′-amino-5′-fluoro-2′-hydroxy-biphenyl-3-carboxylic acid 2f (296 mg, 1.20 mmol) was dissolved in 10 mL of hydrochloric acid (1 N) followed by addition of 10 mL of aqueous sodium nitrite (91 mg, 1.32 mmol) and 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (257 mg, 1.20 mmol). The mixture was adjusted to pH 8 with saturated aqueous sodium bicarbonate, followed by addition of 10 mL of ethanol. The mixture was warmed up to room temperature overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered, dried and recrystallized from methanol to obtain the title compound 5′-fluoro-2′-hydroxy-3′-[N′-(1-indan-5-yl-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-biphenyl-3-carboxylic acid 2 (87 mg, yield 14.1%) as a red solid.

Workup

  1. temperatureUpon cooling by an ice-water bath
  2. filtrationThe mixture was filtered
  3. customdried
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-67f52718da41400a860b7f87ef5b0aa4
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367710B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes