Sodium Bicarbonate → HCID 178433824, compound

HRID 384398Notes

Reaction equation

HRID 384398 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:17])=[C:5]([C:9]2[CH:10]=[C:11]([C:14]([OH:16])=[O:15])[S:12][CH:13]=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.C(O)C>[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[CH:10]=[C:11]([C:14]([OH:16])=[O:15])[S:12][CH:13]=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 574838464-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid hydrobromide

Product 1

HCID 178433824HCID 178433824, compoundYield 10.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

4-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid hydrobromide 51c (80 mg, 0.25 mmol) was dissolved in 1 mL of 1 N hydrochloric acid upon cooling by an ice-water bath, followed by dropwise addition of 0.3 mL of aqueous sodium nitrite (19 mg, 0.28 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 (52 mg, 0.23 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 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 4 mL of ethyl acetate was added to the filter cake. The resulting mixture was stirred for 2 hours and filtered, the filter cake was dried to obtain the title compound 4-(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)-thiophene-2-carboxylic acid 51 (11 mg, yield 10.2%) as a black 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. addition4 mL of ethyl acetate was added to the filter cake
  8. filtrationfiltered
  9. customthe filter cake was dried

Sources & evidence

ORD record
ord-b4709ba7775c49259aeaafbddb303b1c
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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