Sodium Bicarbonate → HCID 178433832, compound

HRID 384393Notes

Reaction equation

HRID 384393 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:41])[N:26]([C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][CH:36]=2)[C:33]([CH3:38])([CH3:37])[CH2:32][C:31]3([CH3:40])[CH3:39])[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:41])[N:26]([C:28]3[CH:29]=[C:30]4[C:34](=[CH:35][CH:36]=3)[C:33]([CH3:38])([CH3:37])[CH2:32][C:31]4([CH3:40])[CH3:39])[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 510369935-Methyl-2-(1,1,3,3-tetramethyl-indan-5-yl)-2,4-dihydro-pyrazol-3-oneHCID 574838145-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid hydrobromide

Product 1

HCID 178433832HCID 178433832, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid hydrobromide 12c (260 mg, 0.823 mmol) was dissolved in 2.7 mL of hydrochloric acid (1 N) upon cooling by an ice-water bath, followed by dropwise addition of 1.1 mL of aqueous sodium nitrite (62 mg, 0.91 mmol). After the mixture was stirred for 20 minutes, 5-methyl-2-(1,1,3,3-tetramethyl-indan-5-yl)-2,4-dihydro-pyrazol-3-one 19d (200 mg, 0.74 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 20 mL of water was added to the filter cake. The mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid and filtered. The filter cake was dried and purified by silica gel column chromatography to obtain the title compound 5-(2-hydroxy-3-{N′-[3-methyl-5-oxo-1-(1,1,3,3-tetramethyl-indan-5-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-thiophene-2-carboxylic acid 49 (216 mg, yield 56.5%) 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. addition20 mL of water was added to the filter cake
  6. filtrationfiltered
  7. customThe filter cake was dried
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-7047de836bb74110b788c6fa8297f145
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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