Sodium Bicarbonate → HCID 178433826, compound

HRID 384326Notes

Reaction equation

HRID 384326 reaction equation
Cl.[NH2:2][C:3]1[C:4]([OH:19])=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=2)[CH:6]=[C:7]([CH3:9])[CH:8]=1.[N:20]([O-])=O.[Na+].[CH3:24][C:25]1[CH2:26][C:27](=[O:40])[N:28]([C:30]2[CH:39]=[CH:38][C:37]3[CH2:36][CH2:35][CH2:34][CH2:33][C:32]=3[CH:31]=2)[N:29]=1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[OH:19][C:4]1[C:3]([NH:2][N:20]=[C:26]2[C:27](=[O:40])[N:28]([C:30]3[CH:39]=[CH:38][C:37]4[CH2:36][CH2:35][CH2:34][CH2:33][C:32]=4[CH:31]=3)[N:29]=[C:25]2[CH3:24])=[CH:8][C:7]([CH3:9])=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=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 574838093'-Amino-2'-hydroxy-5'-methyl-biphenyl-3-carboxylic acid hydrochloride

Product 1

HCID 178433826HCID 178433826, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3′-Amino-2′-hydroxy-5′-methyl-biphenyl-3-carboxylic acid hydrochloride 11f (272 mg, 0.97 mmol) was dissolved in hydrochloric acid (3.3 mL, 1 mol/L) followed by dropwise addition of 1.3 mL of aqueous sodium nitrite (74 mg, 1.07 mmol) upon cooling by an ice-water bath. After the mixture was reacted for 20 minutes, 5-methyl-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-2,4-dihydro-pyrazol-3-one 3i (200 mg, 0.88 mmol), sodium bicarbonate (1.22 g, 14.6 mmol) and 2.1 mL of ethanol were added successively. The reaction mixture was reacted at room temperature for 4 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, filtered and dried to obtain the title compound 2′-hydroxy-5′-methyl-3′-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-biphenyl-3-carboxylic acid 11 (170 mg, yield 40.2%) 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 at room temperature for 4 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. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-bc09943ccf9f4d4fb2b88c9f3822c6a1
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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