Sodium Bicarbonate → HCID 178433803, compound

HRID 384387Notes

Reaction equation

HRID 384387 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:18])=[C:5]([C:10]2[O:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][CH:11]=2)[CH:6]=[C:7]([CH3:9])[CH:8]=1.[N:19]([O-])=O.[Na+].[CH2:23]1[C:31]2[C:26](=[CH:27][C:28]([N:32]3[C:36](=[O:37])[CH2:35][C:34]([CH3:38])=[N:33]3)=[CH:29][CH:30]=2)[CH2:25][CH2:24]1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[OH:18][C:4]1[C:3]([NH:2][N:19]=[C:35]2[C:36](=[O:37])[N:32]([C:28]3[CH:27]=[C:26]4[C:31](=[CH:30][CH:29]=3)[CH2:23][CH2:24][CH2:25]4)[N:33]=[C:34]2[CH3:38])=[CH:8][C:7]([CH3:9])=[CH:6][C:5]=1[C:10]1[O:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574838375-(3-Amino-2-hydroxy-5-methyl-phenyl)-furan-2-carboxylic acid hydrobromide

Product 1

HCID 178433803HCID 178433803, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

5-(3-Amino-2-hydroxy-5-methyl-phenyl)-furan-2-carboxylic acid hydrobromide 46c (219 mg, 0.70 mmol) was dissolved in 2.3 mL of 1 N hydrochloric acid upon cooling by an ice-water bath, followed by dropwise addition of 1.0 mL of aqueous sodium nitrite (53 mg, 0.77 mmol). After the mixture was reacted for 20 minutes, 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (134 mg, 0.63 mmol), sodium bicarbonate (878 mg, 10.45 mmol) and 2 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 the filter cake was added to 20 mL of water. The mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid upon cooling by an ice-water bath. The mixture was filtered and the filter cake was washed with 6 mL of dichloromethane 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]-5-methyl-phenyl}-furan-2-carboxylic acid 46 (170 mg, yield 59.2%) 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. additionthe filter cake was added to 20 mL of water
  6. temperatureupon cooling by an ice-water bath
  7. filtrationThe mixture was filtered
  8. washthe filter cake was washed with 6 mL of dichloromethane
  9. customdried

Sources & evidence

ORD record
ord-2e3273ddaf1e4094854bda7008f0a4a4
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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