Sodium Bicarbonate → HCID 178433796, compound

HRID 384336Notes

Reaction equation

HRID 384336 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+].[CH2:22]1[C:30]2[C:25](=[CH:26][C:27]([N:31]3[C:35](=[O:36])[CH2:34][C:33]([CH3:37])=[N:32]3)=[CH:28][CH:29]=2)[CH2:24][CH2:23]1.C(=O)(O)[O-].[Na+]>Cl>[OH:17][C:4]1[C:3]([NH:2][N:18]=[C:34]2[C:35](=[O:36])[N:31]([C:27]3[CH:26]=[C:25]4[C:30](=[CH:29][CH:28]=3)[CH2:22][CH2:23][CH2:24]4)[N:32]=[C:33]2[CH3:37])=[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 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574838145-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid hydrobromide

Product 1

HCID 178433796HCID 178433796, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid hydrobromide 12c (380 mg, 1.2 mmol) was dissolved in 3.9 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 (90 mg, 1.32 mmol). After the mixture was stirred for 20 minutes, 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (210 mg, 1 mmol) was added. The mixture was adjusted to pH 8˜9 by batch addition of aqueous sodium bicarbonate (1.51 g, 18 mmol). The generated bubbles were quenched with 2 mL of ethanol and 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 20 mL of 5% aqueous sodium hydroxide. The layers were separated and then the aqueous layer was extracted with dichloromethane (50 mL×3). The aqueous layer was adjusted to pH 3˜4 with concentrated hydrochloric acid, filtered and dried. The crude product was purified by HPLC to obtain the title compound 5-{2-hydroxy-3-[N′-(1-indan-5-yl-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-phenyl}-thiophene-2-carboxylic acid 18 (15 mg, yield 3.3%) as an orange solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customThe generated bubbles were quenched with 2 mL of ethanol
  3. customreacted overnight
  4. filtrationThe mixture was filtered
  5. dissolutionthe filter cake was dissolved in 20 mL of 5% aqueous sodium hydroxide
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with dichloromethane (50 mL×3)
  8. filtrationfiltered
  9. customdried
  10. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-a7a701d3eac6476cab9c1eaa041c4511
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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