Sodium Bicarbonate → HCID 178433811, compound

HRID 384333Notes

Reaction equation

HRID 384333 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[CH2:24][C:25](=[O:38])[N:26]([C:28]2[CH:37]=[CH:36][C:35]3[CH2:34][CH2:33][CH2:32][CH2:31][C:30]=3[CH:29]=2)[N:27]=1.C(=O)(O)[O-].[Na+]>Cl>[OH:17][C:4]1[C:3]([NH:2][N:18]=[C:24]2[C:25](=[O:38])[N:26]([C:28]3[CH:37]=[CH:36][C:35]4[CH2:34][CH2:33][CH2:32][CH2:31][C:30]=4[CH:29]=3)[N:27]=[C:23]2[CH3:22])=[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

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 510365803-Methyl-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-1H-pyrazol-5(4H)-oneHCID 574838055-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide

Product 1

HCID 178433811HCID 178433811, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide 9c (292 mg, 0.975 mmol) was dissolved in 3.3 mL of hydrochloric acid (1 N) upon cooling by an ice-water bath, followed by dropwise addition of 1.3 mL of aqueous sodium nitrite (74 mg, 1.07 mmol). After the mixture was stirred for 20 minutes, 5-methyl-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-2,4-dihydro-pyrazol-3-one 3i (200 mg, 0.88 mmol) was added. The mixture was adjusted to pH 8-9 by batch addition of aqueous sodium bicarbonate (1.226 g, 14.6 mmol). The generated bubbles were quenched with 2 mL of ethanol. The reaction mixture was warmed up to room temperature and reacted overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was dissolved in 20 mL of water. After mixing well, the mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid, filtered and dried. The crude product was purified by HPLC to obtain the title compound 5-(2-hydroxy-3-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-furan-2-carboxylic acid 15 (160 mg, yield 39.8%) as a red solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customThe generated bubbles were quenched with 2 mL of ethanol
  3. customreacted overnight
  4. filtrationThe mixture was filtered
  5. dissolutionthe filter cake was dissolved in 20 mL of water
  6. additionAfter mixing well
  7. filtrationfiltered
  8. customdried
  9. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-61ad07e00bf44cd69011b392a48dfbbf
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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