Sodium Bicarbonate → HCID 178433827, compound

HRID 384394Notes

Reaction equation

HRID 384394 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+].[CH3:23][C:24]1[CH2:25][C:26](=[O:39])[N:27]([C:29]2[CH:38]=[CH:37][C:36]3[CH2:35][CH2:34][CH2:33][CH2:32][C:31]=3[CH:30]=2)[N:28]=1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[OH:18][C:4]1[C:3]([NH:2][N:19]=[C:25]2[C:26](=[O:39])[N:27]([C:29]3[CH:38]=[CH:37][C:36]4[CH2:35][CH2:34][CH2:33][CH2:32][C:31]=4[CH:30]=3)[N:28]=[C:24]2[CH3:23])=[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 510365803-Methyl-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-1H-pyrazol-5(4H)-oneHCID 574838375-(3-Amino-2-hydroxy-5-methyl-phenyl)-furan-2-carboxylic acid hydrobromide

Product 1

HCID 178433827HCID 178433827, compoundYield 34.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

5-(3-Amino-2-hydroxy-5-methyl-phenyl)-furan-2-carboxylic acid hydrobromide 46c (120 mg, 0.38 mmol) was dissolved in 1.3 mL of 1 N hydrochloric acid upon cooling by an ice-water bath, followed by dropwise addition of 0.5 mL of aqueous sodium nitrite (29 mg, 0.42 mmol). After the mixture was reacted for 20 minutes, 5-methyl-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-2,4-dihydro-pyrazol-3-one 3i (78 mg, 0.34 mmol) was added. The mixture was adjusted to pH 8 with saturated aqueous sodium bicarbonate followed by addition of 2 mL of ethanol. The reaction mixture was reacted at room temperature overnight. 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. The mixture was filtered and the filter cake was dried and purified by silica gel column chromatography to obtain the title compound 5-(2-hydroxy-5-methyl-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 50 (56 mg, yield 34.8%) 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 at room temperature overnight
  4. filtrationThe mixture was filtered
  5. additionthe filter cake was added to 20 mL of water
  6. filtrationThe mixture was filtered
  7. customthe filter cake was dried
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-cbfe80ee03384bb8993e062093ee9770
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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