Sodium Bicarbonate → HCID 178468731, compound

HRID 384392Notes

Reaction equation

HRID 384392 reaction equation
Br.[CH2:2]([O:4][C:5]([C:7]1[C:11]([CH3:12])=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[C:14]=2[OH:20])[N:9]([CH3:21])[C:8]=1[CH3:22])=[O:6])[CH3:3].[N:23]([O-])=O.[Na+].[CH2:27]1[C:35]2[C:30](=[CH:31][C:32]([N:36]3[C:40](=[O:41])[CH2:39][C:38]([CH3:42])=[N:37]3)=[CH:33][CH:34]=2)[CH2:29][CH2:28]1.C(=O)(O)[O-].[Na+]>Cl>[CH2:2]([O:4][C:5]([C:7]1[C:11]([CH3:12])=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][N:23]=[C:39]3[C:40](=[O:41])[N:36]([C:32]4[CH:31]=[C:30]5[C:35](=[CH:34][CH:33]=4)[CH2:27][CH2:28][CH2:29]5)[N:37]=[C:38]3[CH3:42])[C:14]=2[OH:20])[N:9]([CH3:21])[C:8]=1[CH3:22])=[O:6])[CH3:3]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 686128175-(3-amino-2-hydroxy-phenyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester hydrobromide

Product 1

HCID 178468731HCID 178468731, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-(3-Amino-2-hydroxy-phenyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester hydrobromide 6h (180 mg, 0.66 mmol) was dissolved in 2.2 mL of hydrochloric acid (1 N) upon cooling by an ice-water bath, followed by dropwise addition of 0.8 mL of aqueous sodium nitrite (50 mg, 0.72 mmol). After the mixture was stirred for 20 minutes, 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (126 mg, 0.59 mmol) was added. The mixture was adjusted to pH 8˜9 with saturated aqueous sodium bicarbonate. Then 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 a mixture of 20 mL of chloromethane and 20 mL of water. After mixing well, the mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid. The separated organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 5-{2-hydroxy-3-[N′-(1-indan-5-yl-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-phenyl}-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester 48 (80 mg, yield 25.8%) as a red solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customThen the generated bubbles were quenched with 2 mL of ethanol
  3. customreacted overnight
  4. filtrationThe mixture was filtered
  5. dissolutionthe filter cake was dissolved in a mixture of 20 mL of chloromethane and 20 mL of water
  6. additionAfter mixing well
  7. washThe separated organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customto remove the drying agent
  11. concentrationconcentrated under reduced pressure
  12. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-95aacad497314b4a83992d37d5c7917e
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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