Sodium Bicarbonate → HCID 178435525, compound

HRID 384377Notes

Reaction equation

HRID 384377 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+].[CH2:24]([CH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([N:35]3[C:39](=[O:40])[CH2:38][C:37]([CH3:41])=[N:36]3)[CH:33]=2)[CH2:28][CH2:27]1)[CH3:25].C(=O)(O)[O-].[Na+]>Cl.C(O)C>[CH2:24]([CH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([N:35]3[C:39](=[O:40])[C:38](=[N:20][NH:2][C:3]4[C:4]([OH:19])=[C:5]([C:10]5[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=5)[CH:6]=[C:7]([CH3:9])[CH:8]=4)[C:37]([CH3:41])=[N:36]3)[CH:33]=2)[CH2:28][CH2:27]1)[CH3:25]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837832-(3-Ethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574838093'-Amino-2'-hydroxy-5'-methyl-biphenyl-3-carboxylic acid hydrochloride

Product 1

HCID 178435525HCID 178435525, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3′-Amino-2′-hydroxy-5′-methyl-biphenyl-3-carboxylic acid hydrochloride 11f (298 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 20 mL of water was added to the filter cake. 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-5′-methyl-biphenyl-3-carboxylic acid 42 (290 mg, yield 70.7%) as a red solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. filtrationThe mixture was filtered
  3. addition20 mL of water was added to the filter cake
  4. filtrationThe mixture was filtered
  5. customthe filter cake was dried

Sources & evidence

ORD record
ord-92ee3a71791b4975b080c8626d1beb0f
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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