Sodium Bicarbonate → HCID 178433806, compound

HRID 384322Notes

Reaction equation

HRID 384322 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[CH2:27][C:28](=[O:41])[N:29]([C:31]2[CH:40]=[CH:39][C:38]3[CH2:37][CH2:36][CH2:35][CH2:34][C:33]=3[CH:32]=2)[N:30]=1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[OH:20][C:4]1[C:3]([NH:2][N:21]=[C:27]2[C:26]([CH3:25])=[N:30][N:29]([C:31]3[CH:40]=[CH:39][C:38]4[CH2:37][CH2:36][CH2:35][CH2:34][C:33]=4[CH:32]=3)[C:28]2=[O:41])=[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 510365803-Methyl-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-1H-pyrazol-5(4H)-oneHCID 178479035HCID 178479035, compound

Product 1

HCID 178433806HCID 178433806, compoundYield 34.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3-Amino-3′-(1H-tetrazol-5-yl)-biphenyl-2-ol hydrochloride 8f (340 mg, 1.34 mmol) was dissolved in 3 mL of 1 N hydrochloric acid followed by dropwise addition of 3 mL of aqueous sodium nitrite (98 mg, 1.41 mmol) upon cooling by an ice-water bath. After the mixture was reacted for 10 minutes, 5-methyl-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-2,4-dihydro-pyrazol-3-one 3i (276 mg, 1.21 mmol), sodium bicarbonate (1.69 g, 20 mmol) and 3 mL of ethanol were added successively. The reaction mixture was reacted at room temperature for 18 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 3˜4 with concentrated hydrochloric acid. Then the mixture was filtered and dried to obtain the title compound 4-{[2-hydroxy-3′-(1H-tetrazol-5-yl)-biphenyl-3-yl]-hydrazono}-5-methyl-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-2,4-dihydro-pyrazol-3-one 10 (208 mg, 31.6%) as a yellow solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customAfter the mixture was reacted for 10 minutes
  3. customThe reaction mixture was reacted at room temperature for 18 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. filtrationThen the mixture was filtered
  9. customdried

Sources & evidence

ORD record
ord-aa1cf1dba57c449998248a0875695af4
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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