Sodium Bicarbonate → HCID 178433844, compound

HRID 384310Notes

Reaction equation

HRID 384310 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+].[O:23]1[C:27]2[CH:28]=[CH:29][C:30]([N:32]3[C:36](=[O:37])[CH2:35][C:34]([CH3:38])=[N:33]3)=[CH:31][C:26]=2[CH2:25][CH2:24]1.C(=O)(O)[O-].[Na+]>Cl>[O:23]1[C:27]2[CH:28]=[CH:29][C:30]([N:32]3[C:36](=[O:37])[C:35](=[N:19][NH:2][C:3]4[C:4]([OH:18])=[C:5]([C:9]5[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=5)[CH:6]=[CH:7][CH:8]=4)[C:34]([CH3:38])=[N:33]3)=[CH:31][C:26]=2[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837812-(2,3-Dihydro-benzofuran-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574837893'-Amino-2'-hydroxy-biphenyl-3-carboxylic acid hydrobromide

Product 1

HCID 178433844HCID 178433844, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

3′-Amino-2′-hydroxy-biphenyl-3-carboxylic acid hydrobromide 1f (155 mg, 0.5 mmol) was dissolved in 1.7 mL of hydrochloric acid (1 N) followed by dropwise addition of 0.6 mL of aqueous sodium nitrite (36 mg, 0.53 mmol) and the mixture was stirred for 10 minutes upon cooling by an ice-water bath. Then 2-(2,3-dihydro-benzofuran-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 7c (97 mg, 0.45 mmol) was added. The mixture was adjusted to pH 7 by batch addition of saturated aqueous sodium bicarbonate (630 mg, 7.5 mmol). The reaction mixture was warmed up to room temperature overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was adjusted to pH<5 with concentrated hydrochloric acid. The mixture was filtered and dried to obtain the title compound 3′-{N′-[1-(2,3-dihydro-benzofuran-5-yl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-2′-hydroxy-biphenyl-3-carboxylic acid 7 (131 mg, yield 63.9%) as a brown solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. filtrationThe mixture was filtered
  3. customdried

Sources & evidence

ORD record
ord-e1d504f560d94279b1c5c9c48bc145b6
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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