Sodium Bicarbonate → HCID 178433787, compound

HRID 384360Notes

Reaction equation

HRID 384360 reaction equation
[OH:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][CH2:17][CH2:18][N:19]=2)=[CH:11][CH:10]=1.[N:20]([O-])=O.[Na+].[CH2:24]1[C:32]2[C:27](=[CH:28][C:29]([N:33]3[C:37](=[O:38])[CH2:36][C:35]([CH3:39])=[N:34]3)=[CH:30][CH:31]=2)[CH2:26][CH2:25]1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[NH:19]1[CH2:18][CH2:17][N:16]=[C:15]1[C:12]1[CH:11]=[CH:10][C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([NH:8][N:20]=[C:36]3[C:35]([CH3:39])=[N:34][N:33]([C:29]4[CH:28]=[C:27]5[C:32](=[CH:31][CH:30]=4)[CH2:24][CH2:25][CH2:26]5)[C:37]3=[O:38])[C:2]=2[OH:1])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 136006496HCID 136006496, compound

Product 1

HCID 178433787HCID 178433787, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

2-(2′-Hydroxy-3′-amino-biphenyl-4-yl-4,5-dihydro-1H-imidazol 32d (334 mg, 1.11 mmol) was dissolved in hydrochloric acid (3.7 mL, 1 mol/L) upon cooling by an ice-water bath, followed by dropwise addition of 1.5 mL of aqueous sodium nitrite (85 mg, 1.22 mmol). After the mixture was reacted for 20 minutes, 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (214 mg, 1 mmol) was added. The mixture was adjusted to pH 8 with saturated aqueous sodium bicarbonate, followed by addition of 5 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 30 mL of water was added to the filter cake. After mixing well, the mixture was adjusted to pH 4 with concentrated hydrochloric acid to form precipitates. The mixture was filtered and the filter cake was purified by silica gel column chromatography to obtain the title compound 4-{[4′-(4,5-dihydro-1H-imidazol-2-yl)-2-hydroxy-biphenyl-3-yl]-hydrazono}-2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 32 (145 mg, yield 30.3%) 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. addition30 mL of water was added to the filter cake
  6. additionAfter mixing well
  7. customto form
  8. customprecipitates
  9. filtrationThe mixture was filtered
  10. customthe filter cake was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5e0fba0ec4974344b00d926f864ea9fc
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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