Sodium Bicarbonate → HCID 178433804, compound

HRID 384345Notes

Reaction equation

HRID 384345 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:18])=[C:5]([C:10]2[S:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][CH:11]=2)[CH:6]=[C:7]([CH3:9])[CH:8]=1.[N:19]([O-])=O.[Na+].[CH2:23]1[C:31]2[C:26](=[CH:27][C:28]([N:32]3[C:36](=[O:37])[CH2:35][C:34]([CH3:38])=[N:33]3)=[CH:29][CH:30]=2)[CH2:25][CH2:24]1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[OH:18][C:4]1[C:3]([NH:2][N:19]=[C:35]2[C:36](=[O:37])[N:32]([C:28]3[CH:27]=[C:26]4[C:31](=[CH:30][CH:29]=3)[CH2:23][CH2:24][CH2:25]4)[N:33]=[C:34]2[CH3:38])=[CH:8][C:7]([CH3:9])=[CH:6][C:5]=1[C:10]1[S:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574838215-(3-Amino-2-hydroxy-5-methyl-phenyl)-thiophene-2-carboxylic acid hydrobromide

Product 1

HCID 178433804HCID 178433804, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

5-(3-Amino-2-hydroxy-5-methyl-phenyl)-thiophene-2-carboxylic acid hydrobromide 24d (138 mg, 0.42 mmol) was dissolved in 1.5 mL of 1 N hydrochloric acid 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 reacted for 20 minutes, 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (81 mg, 0.38 mmol), sodium bicarbonate (527 mg, 6.27 mmol) and 2 mL of ethanol were added successively. The reaction mixture was reacted overnight at room temperature. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was washed with 20 mL of water, and then dissolved in 10 mL of water. Upon cooling by an ice-water bath, the mixture was adjusted to pH 3-4 with concentrated hydrochloric acid, filtered and dried 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]-5-methyl-phenyl}-thiophene-2-carboxylic acid 24 (30 mg, yield 16.7%) as a red solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customAfter the mixture was reacted for 20 minutes
  3. customThe reaction mixture was reacted overnight at room temperature
  4. filtrationThe mixture was filtered
  5. washthe filter cake was washed with 20 mL of water
  6. dissolutiondissolved in 10 mL of water
  7. temperatureUpon cooling by an ice-water bath
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-24f1f57ca42942e0a33e4ad2833f51c5
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

Loading…