Sodium Bicarbonate → HCID 178433834, compound

HRID 384317Notes

Reaction equation

HRID 384317 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+].[CH3:25][C:26]1([CH3:42])[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([N:35]3[C:39](=[O:40])[CH2:38][C:37]([CH3:41])=[N:36]3)[CH:33]=2)[CH2:28][CH2:27]1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[CH3:25][C:26]1([CH3:42])[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([N:35]3[C:39](=[O:40])[C:38](=[N:21][NH:2][C:3]4[C:4]([OH:20])=[C:5]([C:9]5[CH:14]=[CH:13][CH:12]=[C:11]([C:15]6[NH:19][N:18]=[N:17][N:16]=6)[CH:10]=5)[CH:6]=[CH:7][CH:8]=4)[C:37]([CH3:41])=[N:36]3)[CH:33]=2)[CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 510369942-(3,3-Dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 178479035HCID 178479035, compound

Product 1

HCID 178433834HCID 178433834, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3-Amino-3′-(1H-tetrazol-5-yl)-biphenyl-2-ol hydrochloride 8f (290 mg, 1.0 mmol) was dissolved in hydrochloric acid (3.4 mL, 1 mol/L) followed by dropwise addition of 1.2 mL of aqueous sodium nitrite (73 mg, 1.05 mmol) upon cooling by an ice-water bath. After the mixture was reacted at room temperature for 10 minutes, 2-(3,3-dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 8i (218 mg, 0.9 mmol), sodium bicarbonate (1.26 g, 15 mmol) and 4.4 mL of ethanol were added successively. Then the reaction mixture was reacted for 10 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was washed with 20 mL of water and then dissolved in 20 mL of water. Upon cooling by an ice-water bath, the mixture was adjusted to pH<5 with concentrated hydrochloric acid. The mixture was filtered and dried to obtain the title compound 2-(3,3-dimethyl-indan-5-yl)-4-{[2-hydroxy-3′-(1H-tetrazol-5-yl)-biphenyl-3-yl]-hydrazono}-5-methyl-2,4-dihydro-pyrazol-3-one 8 (336 mg, yield 73.8%) as a yellow solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customAfter the mixture was reacted at room temperature for 10 minutes
  3. customThen the reaction mixture was reacted for 10 hours
  4. filtrationThe mixture was filtered
  5. washthe filter cake was washed with 20 mL of water
  6. dissolutiondissolved in 20 mL of water
  7. temperatureUpon cooling by an ice-water bath
  8. filtrationThe mixture was filtered
  9. customdried

Sources & evidence

ORD record
ord-782c158e945448b999a83ab377786852
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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