Sodium Bicarbonate → HCID 178433808, compound

HRID 384298Notes

Reaction equation

HRID 384298 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:18])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[N:19]([O-])=O.[Na+].[CH3:23][C:24]1[CH2:25][C:26](=[O:39])[N:27]([C:29]2[CH:38]=[CH:37][C:36]3[CH2:35][CH2:34][CH2:33][CH2:32][C:31]=3[CH:30]=2)[N:28]=1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[OH:18][C:4]1[C:3]([NH:2][N:19]=[C:25]2[C:26](=[O:39])[N:27]([C:29]3[CH:38]=[CH:37][C:36]4[CH2:35][CH2:34][CH2:33][CH2:32][C:31]=4[CH:30]=3)[N:28]=[C:24]2[CH3:23])=[CH:8][CH:7]=[CH:6][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[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 574837893'-Amino-2'-hydroxy-biphenyl-3-carboxylic acid hydrobromide

Product 1

HCID 178433808HCID 178433808, compoundYield 11.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Upon cooling by an ice-water bath, 3′-amino-2′-hydroxy-biphenyl-3-carboxylic acid hydrobromide 1f (250 mg, 1.09 mmol) was dissolved in 10 mL of hydrochloric acid (1 N) followed by addition of 10 mL of aqueous sodium nitrite (82 mg, 1.2 mmol) and 5-methyl-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-2,4-dihydro-pyrazol-3-one 3i (249 mg, 1.09 mmol). Then the mixture was adjusted to pH 8 with saturated aqueous sodium bicarbonate, followed by addition of 10 mL of ethanol. The reaction was warmed up to room temperature overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered, dried and recrystallized from methanol to obtain the title compound 2′-hydroxy-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 3 (59 mg, yield 11.6%) as a yellow solid.

Workup

  1. temperatureUpon cooling by an ice-water bath
  2. filtrationThe mixture was filtered
  3. customdried
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5b88644628874ab998773c82842cb156
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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