Sodium Bicarbonate → HCID 178433838, compound

HRID 384378Notes

Reaction equation

HRID 384378 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 178433838HCID 178433838, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

5-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide 9c (333 mg, 1.1 mmol) was dissolved in hydrochloric acid (3.7 mL, 1 mol/L) 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-(3,3-dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 8i (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 reaction was monitored by TLC until the disappearance of the starting materials. 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 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 43 (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-f2a75fd1da37468b9980e8cc2be3a8ff
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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