Sodium Bicarbonate → HCID 178433818, compound

HRID 384405Notes

Reaction equation

HRID 384405 reaction equation
Br.[OH:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[O:14][C:13]([CH3:15])=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=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:2][C:3]1[C:8]([NH:9][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:7][CH:6]=[CH:5][C:4]=1[C:10]1[O:14][C:13]([CH3:15])=[C:12]([C:16]([OH:18])=[O:17])[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 57483852HCID 57483852, compound

Product 1

HCID 178433818HCID 178433818, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

5-(2-Hydroxy-3-amino-phenyl)-2-methyl-furan-3-carboxylic acid hydrobromide 53e (200 mg, 0.64 mmol) was dissolved in 2.2 mL of 1 N hydrochloric acid upon cooling by an ice-water bath, followed by dropwise addition of 0.9 mL of aqueous sodium nitrite (48 mg, 0.7 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 (131 mg, 0.57 mmol) was added. The mixture was adjusted to pH 8 with saturated aqueous sodium bicarbonate followed by addition of 2 mL ethanol. 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. The mixture was filtered and 8 mL of ethyl acetate was added to the filter cake. After stirring for 1 hour, the mixture was filtered and the filter cake was dried 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)-2-methyl-furan-3-carboxylic acid 53 (200 mg, yield 73.8%) 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 overnight at room temperature
  4. filtrationThe mixture was filtered
  5. additionthe filter cake was added to 20 mL of water
  6. filtrationThe mixture was filtered
  7. addition8 mL of ethyl acetate was added to the filter cake
  8. filtrationthe mixture was filtered
  9. customthe filter cake was dried

Sources & evidence

ORD record
ord-6c8832f32a574d34bec4a393493d386f
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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