Sodium Bicarbonate → (1,1'-Biphenyl)-3-carboxylic acid

HRID 384370Notes

Reaction equation

HRID 384370 reaction equation
Cl.[NH2:2][C:3]1[C:4]([OH:19])=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=2)[CH:6]=[C:7]([CH3:9])[CH:8]=1.[N:20]([O-])=O.[Na+].[CH3:24][C:25]1[CH2:26][C:27](=[O:40])[N:28]([C:30]2[CH:31]=[C:32]3[C:36](=[CH:37][CH:38]=2)[CH2:35][CH2:34][CH:33]3[CH3:39])[N:29]=1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[OH:19][C:4]1[C:3]([NH:2][N:20]=[C:26]2[C:27](=[O:40])[N:28]([C:30]3[CH:31]=[C:32]4[C:36](=[CH:37][CH:38]=3)[CH2:35][CH2:34][CH:33]4[CH3:39])[N:29]=[C:25]2[CH3:24])=[CH:8][C:7]([CH3:9])=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=1.[C:10]1([C:5]2[CH:6]=[CH:7][CH:8]=[CH:3][CH:4]=2)[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837825-Methyl-2-(3-methyl-indan-5-yl)-2,4-dihydro-pyrazol-3-oneHCID 574838093'-Amino-2'-hydroxy-5'-methyl-biphenyl-3-carboxylic acid hydrochloride

Product 2

HCID 12854(1,1'-Biphenyl)-3-carboxylic acidYield 218.2%HCID 178433825HCID 178433825, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3′-Amino-2′-hydroxy-5′-methyl-biphenyl-3-carboxylic acid hydrochloride 11f (360 mg, 1.11 mmol) was dissolved in 3.7 mL of hydrochloric acid (1 N) upon cooling by an ice-water bath, followed by dropwise addition of 1.5 mL of aqueous sodium nitrite (85 mg, 1.22 mmol). After the mixture was stirred for 20 minutes, 5-methyl-2-(3-methyl-indan-5-yl)-2,4-dihydro-pyrazol-3-one 38f (228 mg, 1.0 mmol) was added. The mixture was adjusted to pH 8 with saturated aqueous sodium bicarbonate, followed by addition of 2 mL ethanol. The reaction mixture was warmed up to room temperature and reacted overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was dissolved in 30 mL of water. After mixing well, the mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid. The mixture was filtered and the filter cake was dried followed by addition of 10 mL dichloromethane. The mixture was stirred for 1 hour and filtered. The filter cake was dried to obtain the title compound 2′-hydroxy-5′-methyl-3′-{N′-[3-methyl-1-methyl-indan-5-yl)-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-biphenyl-3-carboxylic acid 39 (240 mg, yield 49.8%) as a red solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customreacted overnight
  3. filtrationThe mixture was filtered
  4. dissolutionthe filter cake was dissolved in 30 mL of water
  5. additionAfter mixing well
  6. filtrationThe mixture was filtered
  7. customthe filter cake was dried
  8. additionfollowed by addition of 10 mL dichloromethane
  9. stirringThe mixture was stirred for 1 hour
  10. filtrationfiltered
  11. customThe filter cake was dried

Sources & evidence

ORD record
ord-3c7ccc98c49e4d148d9e8b7065eaa8a7
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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