Sodium Bicarbonate → HCID 178433788, compound

HRID 384348Notes

Reaction equation

HRID 384348 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[NH:19][N:18]=[N:17][N:16]=3)[CH:10]=2)[C:4]=1[OH:20].[N:21]([O-])=O.[Na+].[CH2:25]1[C:33]2[C:28](=[CH:29][C:30]([N:34]3[C:38](=[O:39])[CH2:37][C:36]([CH3:40])=[N:35]3)=[CH:31][CH:32]=2)[CH2:27][CH2:26]1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[OH:20][C:4]1[C:3]([NH:2][N:21]=[C:37]2[C:36]([CH3:40])=[N:35][N:34]([C:30]3[CH:29]=[C:28]4[C:33](=[CH:32][CH:31]=3)[CH2:25][CH2:26][CH2:27]4)[C:38]2=[O:39])=[CH:8][CH:7]=[CH:6][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[NH:19][N:18]=[N:17][N:16]=2)[CH:10]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 178479035HCID 178479035, compound

Product 1

HCID 178433788HCID 178433788, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3-Amino-3′-(1H-tetrazol-5-yl)-biphenyl-2-ol hydrochloride 8f (188 mg, 0.74 mmol) was dissolved in 4 mL of 2 N hydrochloric acid upon cooling by an ice-water bath, followed by dropwise addition of 1 mL of aqueous sodium nitrite (57 mg, 0.82 mmol). After the mixture was reacted for 30 minutes, 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (159 mg, 0.74 mmol) was added. The mixture was adjusted to pH 8 with saturated sodium bicarbonate, followed by addition of 0.5 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 the filter cake was dissolved in aqueous sodium hydroxide (3 N). The mixture was washed three times with dichloromethane. The layers were separated and then the aqueous layer was adjusted to pH 3 with 2 N hydrochloric acid to form a copious amount of precipitates. The mixture was filtered and the filter cake was purified by silica gel column chromatography to obtain the title compound 4-{[2-hydroxy-3′-(1H-tetrazol-5-yl)-biphenyl-3-yl]-hydrazono}-2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 27 (67 mg, yield 18.8%) as an orange solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customAfter the mixture was reacted for 30 minutes
  3. customThe reaction mixture was reacted overnight at room temperature
  4. filtrationThe mixture was filtered
  5. dissolutionthe filter cake was dissolved in aqueous sodium hydroxide (3 N)
  6. washThe mixture was washed three times with dichloromethane
  7. customThe layers were separated
  8. customto form a copious amount
  9. customof precipitates
  10. filtrationThe mixture was filtered
  11. customthe filter cake was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0b6deb530479409096cc3f999b417323
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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