Sodium Bicarbonate → HCID 178433798, compound

HRID 384356Notes

Reaction equation

HRID 384356 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:17])=[C:5]([C:9]2[CH:10]=[C:11]([C:14]([OH:16])=[O:15])[O:12][CH:13]=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.C(O)C>[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[CH:10]=[C:11]([C:14]([OH:16])=[O:15])[O:12][CH:13]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574838264-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide

Product 1

HCID 178433798HCID 178433798, compoundYield 36.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

4-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide 28e (170 mg, 0.57 mmol) was dissolved in hydrochloric acid (1.9 mL, 1 mol/L) upon cooling by an ice-water bath, followed by dropwise addition of 0.7 mL of aqueous sodium nitrite (43 mg, 0.63 mmol). After the mixture was reacted for 20 minutes, 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (109 mg, 0.51 mmol) was added. The mixture was adjusted to pH 8˜9 with saturated aqueous sodium bicarbonate, followed by addition of 2 mL of ethanol. The reaction mixture was reacted at room temperature for 24 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and 15 mL of water was added to the filter cake. Upon cooling by an ice-water bath, the mixture was adjusted to pH 2˜3 with concentrated hydrochloric acid, filtered and the filter cake was washed with ethyl acetate, and then dried to obtain the title compound 4-{2-hydroxy-3-[N′-(1-indan-5-yl-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-phenyl}-furan-2-carboxylic acid 31 (83 mg, yield 36.7%) as a black 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 at room temperature for 24 hours
  4. filtrationThe mixture was filtered
  5. addition15 mL of water was added to the filter cake
  6. temperatureUpon cooling by an ice-water bath
  7. filtrationfiltered
  8. washthe filter cake was washed with ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-d12c19096f614e4da6b1bc68d4776591
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

Loading…