Sodium Bicarbonate → HCID 178433839, compound

HRID 384383Notes

Reaction equation

HRID 384383 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+].[CH3:22][C:23]1([CH3:39])[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([N:32]3[C:36](=[O:37])[CH2:35][C:34]([CH3:38])=[N:33]3)[CH:29]=2)[CH2:24]1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[CH3:22][C:23]1([CH3:39])[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([N:32]3[C:36](=[O:37])[C:35](=[N:18][NH:2][C:3]4[C:4]([OH:17])=[C:5]([C:9]5[O:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=5)[CH:6]=[CH:7][CH:8]=4)[C:34]([CH3:38])=[N:33]3)[CH:29]=2)[CH2:24]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837842-(2,2-Dimethyl-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 178433839HCID 178433839, compoundYield 31.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

5-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide 9c (150 mg, 0.5 mmol) was dissolved in hydrochloric acid (1.7 mL, 1 mol/L) upon cooling by an ice-water bath, followed by dropwise addition of 0.6 mL of aqueous sodium nitrite (38 mg, 0.55 mmol). After the mixture was reacted for 20 minutes, 2-(2,2-dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 45d (109 mg, 0.45 mmol), sodium bicarbonate (630 mg, 7.5 mmol) and 1 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 15 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 washed with ethyl acetate (1 mL×3) and dried to obtain the title compound 5-(3-{N′-[1-(2,2-dimethyl-indan-5-yl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-2-hydroxy-phenyl)-furan-2-carboxylic acid 45 (67 mg, yield 31.6%) as a yellow 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. addition15 mL of water was added to the filter cake
  6. filtrationfiltered
  7. washThe filter cake was washed with ethyl acetate (1 mL×3)
  8. customdried

Sources & evidence

ORD record
ord-e0becc5e2c1b47ce8cc8e8aa1c73e38f
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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