Sodium Bicarbonate → HCID 178433816, compound

HRID 384371Notes

Reaction equation

HRID 384371 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:17])=[C:5]([C:9]2[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[N:18]([O-])=O.[Na+].[CH3:22][C:23]1[CH2:24][C:25](=[O:38])[N:26]([C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][CH:36]=2)[CH2:33][CH2:32][CH:31]3[CH3:37])[N:27]=1.C(=O)(O)[O-].[Na+]>Cl>[OH:17][C:4]1[C:3]([NH:2][N:18]=[C:24]2[C:25](=[O:38])[N:26]([C:28]3[CH:29]=[C:30]4[C:34](=[CH:35][CH:36]=3)[CH2:33][CH2:32][CH:31]4[CH3:37])[N:27]=[C:23]2[CH3:22])=[CH:8][CH:7]=[CH:6][C:5]=1[C:9]1[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837825-Methyl-2-(3-methyl-indan-5-yl)-2,4-dihydro-pyrazol-3-oneHCID 574838145-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid hydrobromide

Product 1

HCID 178433816HCID 178433816, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid hydrobromide 12c (351 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 mmol) was added. The mixture was adjusted to pH 8 with saturated aqueous sodium bicarbonate. Then the generated bubbles were quenched with 2 mL of ethanol. The reaction mixture was warmed up to room temperature and reacted for 3 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and 30 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, and then purified by silica gel column chromatography to obtain the title compound 5-(2-hydroxy-3-{N′-[3-methyl-1-(3-methyl-indan-5-yl)-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-thiophene-2-carboxylic acid 40 (90 mg, yield 19.0%) as a red solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customThen the generated bubbles were quenched with 2 mL of ethanol
  3. customreacted for 3 hours
  4. filtrationThe mixture was filtered
  5. addition30 mL of water was added to the filter cake
  6. filtrationThe mixture was filtered
  7. customthe filter cake was dried
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-faf364f916a34b938b6011c0b99378cc
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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