Sodium Bicarbonate → HCID 178433800, compound

HRID 384399Notes

Reaction equation

HRID 384399 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+].[CH2:22]1[C:30]2[C:25](=[CH:26][C:27]([N:31]3[C:35](=[O:36])[CH2:34][C:33]([CH3:37])=[N:32]3)=[CH:28][CH:29]=2)[CH2:24][CH2:23]1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[OH:17][C:4]1[C:3]([NH:2][N:18]=[C:34]2[C:35](=[O:36])[N:31]([C:27]3[CH:26]=[C:25]4[C:30](=[CH:29][CH:28]=3)[CH2:22][CH2:23][CH2:24]4)[N:32]=[C:33]2[CH3:37])=[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 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574838464-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid hydrobromide

Product 1

HCID 178433800HCID 178433800, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

4-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid hydrobromide 51c (120 mg, 0.38 mmol) was dissolved in 2.7 mL of 1 N hydrochloric acid upon cooling by an ice-water bath, followed by dropwise addition of 0.45 mL of aqueous sodium nitrite (29 mg, 0.42 mmol). After the mixture was reacted for 20 minutes, 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (73 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 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 and filtered. Then 5 mL of ethyl acetate was added to the filter cake and the mixture was stirred for 1 hour. The mixture was filtered and the filter cake was dried to obtain the title compound 4-{2-hydroxy-3-[N′-(1-indan-5-yl-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-phenyl}-thiophene-2-carboxylic acid 52 (45 mg, yield 28.7%) as a yellow 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. filtrationfiltered
  7. additionThen 5 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-0cd32a1b85484d00b9f4523f2f4d2d96
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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