Sodium Bicarbonate → HCID 178433794, compound

HRID 384321Notes

Reaction equation

HRID 384321 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:17])=[C:5]([C:9]2[O: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.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[O:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574838055-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide

Product 1

HCID 178433794HCID 178433794, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

5-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide 9c (300 mg, 1.0 mmol) was dissolved in hydrochloric acid (3.4 mL, 1 mol/L) followed by dropwise addition of 1.2 mL of aqueous sodium nitrite (73 mg, 1.05 mmol) upon cooling by an ice-water bath. After the mixture was reacted for 10 minutes, 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (193 mg, 0.9 mmol), sodium bicarbonate (1.26 g, 15 mmol) and 4.4 mL of ethanol were added successively. The 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 the filter cake was washed with 20 mL of water and then dissolved in 20 mL of water. Upon cooling by an ice-water bath, the mixture was adjusted to pH<5 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]-phenyl}-furan-2-carboxylic acid 9 (287 mg, yield 71.8%) as a yellow solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customAfter the mixture was reacted for 10 minutes
  3. customThe mixture was reacted at room temperature for 24 hours
  4. filtrationThe mixture was filtered
  5. washthe filter cake was washed with 20 mL of water
  6. dissolutiondissolved in 20 mL of water
  7. temperatureUpon cooling by an ice-water bath
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-bb8dd43462af46c3811dd0b27738df8d
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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