Sodium Bicarbonate → HCID 178433837, compound

HRID 238707Notes

Reaction equation

HRID 238707 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])[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([N:32]3[C:36](=[O:37])[CH2:35][C:34]([CH3:38])=[N:33]3)[CH:30]=2)[CH2:25][CH2:24]1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[CH3:22][C:23]1([CH3:39])[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([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:30]=2)[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 510369942-(3,3-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 178433837HCID 178433837, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

(Z)-5-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide 4g (333 mg, 1.1 mmol) was dissolved in hydrochloric acid (3.7 mL, 1 M) upon cooling by an ice-water bath, followed by dropwise addition of 1.5 mL of sodium nitrite solution (85 mg, 1.22 mmol). After the mixture was reacted for 20 minutes, 2-(3,3-dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 4c (242 mg, 1.0 mmol), sodium bicarbonate (1.4 g, 16.67 mmol) and 3 mL of ethanol were added successively. The reaction mixture was reacted overnight at room temperature. The mixture was filtered and 20 mL of water was added to the filter cake. The mixture was adjusted to pH 3-4 with concentrated hydrochloric acid. The mixture was filtered and the filter cake was dried and purified by silica gel column chromatography to obtain the title compound (Z)-5-(3-{N′-[1-(3,3-dimethyl-indan-5-yl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-2-hydroxy-phenyl)-furan-2-carboxylic acid 4h (190 mg, yield 40.3%) 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. addition20 mL of water was added to the filter cake
  6. filtrationThe mixture was filtered
  7. customthe filter cake was dried
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-afd206792f8348779d489caeebd13222
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Reaction notes

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