Sodium Bicarbonate → HCID 178435524, compound

HRID 384376Notes

Reaction equation

HRID 384376 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]([CH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([N:34]3[C:38](=[O:39])[CH2:37][C:36]([CH3:40])=[N:35]3)[CH:32]=2)[CH2:27][CH2:26]1)[CH3:24].C(=O)(O)[O-].[Na+]>Cl.C(O)C>[CH2:23]([CH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([N:34]3[C:38](=[O:39])[C:37](=[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:36]([CH3:40])=[N:35]3)[CH:32]=2)[CH2:27][CH2:26]1)[CH3:24]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837832-(3-Ethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574837893'-Amino-2'-hydroxy-biphenyl-3-carboxylic acid hydrobromide

Product 1

HCID 178435524HCID 178435524, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3′-Amino-2′-hydroxy-biphenyl-3-carboxylic acid hydrobromide 1f (285 mg, 0.92 mmol) was dissolved in 3.1 mL of hydrochloric acid (1 N) upon cooling by an ice-water bath, followed by dropwise addition of 1.2 mL of aqueous sodium nitrite (70 mg, 1.01 mmol). After the mixture was stirred for 20 minutes, 2-(3-ethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 41d (200 mg, 0.83 mmol) was added. The mixture was adjusted to pH 8 with saturated aqueous sodium bicarbonate followed by addition of 2 mL of ethanol. 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 filtered and the filter cake was added to 20 mL of water. The mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid. The mixture was filtered and the filter cake was dried to obtain the title compound 3′-{N′-[1-(3-ethyl-indan-5-yl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-2′-hydroxy-biphenyl-3-carboxylic acid 41 (145 mg, yield 36.4%) as a red solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. filtrationThe mixture was filtered
  3. additionthe filter cake was added to 20 mL of water
  4. filtrationThe mixture was filtered
  5. customthe filter cake was dried

Sources & evidence

ORD record
ord-9306d1c560ad4668afc3926e4a694efd
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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