Sodium Bicarbonate → 3-[3-[(2Z)-2-[1-(2,3-dihydro-1H-inden-5-yl)-3-methyl-5-(oxomethylidene)pyrazol-4-ylidene]hydrazinyl]-2-hydroxyphenyl]benzoic acid

HRID 238699Notes

Reaction equation

HRID 238699 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:18])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=2)[CH:6]=[CH:7][CH:8]=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:39](=[O:42])(O)[O-].[Na+]>Cl.C(O)C>[OH:18][C:4]1[C:3]([NH:2]/[N:19]=[C:35]2/[C:34]([CH3:38])=[N:33][N:32]([C:28]3[CH:27]=[C:26]4[C:31](=[CH:30][CH:29]=3)[CH2:23][CH2:24][CH2:25]4)[C:36]/2=[O:37])=[CH:8][CH:7]=[CH:6][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=1.[OH:18][C:4]1[C:3]([NH:2]/[N:19]=[C:35]2\[C:34]([CH3:38])=[N:33][N:32]([C:28]3[CH:27]=[C:26]4[C:31](=[CH:30][CH:29]=3)[CH2:23][CH2:24][CH2:25]4)[C:36]\2=[C:39]=[O:42])=[CH:8][CH:7]=[CH:6][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574837893'-Amino-2'-hydroxy-biphenyl-3-carboxylic acid hydrobromide

Product 2

HCID 1765211573-[3-[(2Z)-2-[1-(2,3-dihydro-1H-inden-5-yl)-3-methyl-5-(oxomethylidene)pyrazol-4-ylidene]hydrazinyl]-2-hydroxyphenyl]benzoic acidYield 11.4%HCID 178433789HCID 178433789, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Upon cooling by an ice-water bath, 3′-amino-2′-hydroxy-biphenyl-3-carboxylic acid hydrobromide 1f (267 mg, 1.16 mmol) was dissolved in 10 mL of 1M hydrochloric acid followed by dropwise addition of 10 mL of sodium nitrite solution (88 mg, 1.28 mmol) and 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (249 mg, 1.16 mmol). The mixture was adjusted to pH 8 with saturated sodium bicarbonate solution, followed by addition of 10 mL of ethanol. The reaction mixture was warmed up to room temperature overnight. The mixture was filtered, dried and recrystallized from methanol to obtain the title compound (Z)-2′-hydroxy-3′-[N′-(1-indan-5-yl-3-methyl-5-carbonyl-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-biphenyl-3-carboxylic acid 1j (60 mg, yield 11.4%) as a yellow 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-2d68a287958c4ec4b2a7a96acc35eda3
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Reaction notes

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