Sodium Bicarbonate → HCID 178433807, compound

HRID 384369Notes

Reaction equation

HRID 384369 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:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[CH2:34][CH2:33][CH:32]3[CH3:38])[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:30]=[C:31]4[C:35](=[CH:36][CH:37]=3)[CH2:34][CH2:33][CH:32]4[CH3:38])[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 574837825-Methyl-2-(3-methyl-indan-5-yl)-2,4-dihydro-pyrazol-3-oneHCID 574837893'-Amino-2'-hydroxy-biphenyl-3-carboxylic acid hydrobromide

Product 1

HCID 178433807HCID 178433807, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3′-Amino-2′-hydroxy-biphenyl-3-carboxylic acid hydrobromide 1f (344 mg, 1.11 mmol) was dissolved in 3.7 mL of hydrochloric acid (1 N) upon cooling by an ice-water bath, followed by addition of 1.5 mL of aqueous sodium nitrite (85 mg, 1.22 mmol) and 5-methyl-2-(3-methyl-indan-5-yl)-2,4-dihydro-pyrazol-3-one 38f (228 mg, 1 mmol). The mixture was adjusted to pH 8 with saturated aqueous sodium bicarbonate, followed by addition of 2 mL of ethanol. The reaction mixture was warmed up to room temperature overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and 30 mL of water was added to the filter cake. The mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid and filtered. The filter cake was dried and then 10 mL of a solvent mixture of dichloromethane/methanol (V:V=50:1) was added. Upon completion of the addition, the mixture was stirred for 1 hour. Then the mixture was filtered and the filter cake was washed with dichloromethane (2 mL×3) and dried to obtain the title compound 2′-hydroxy-3′-{N′-[3-methyl-1-(3-methyl-indan-5-yl)-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-biphenyl-3-carboxylic acid 38 (300 mg, yield 64.1%) as a yellow solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. filtrationThe mixture was filtered
  3. addition30 mL of water was added to the filter cake
  4. filtrationfiltered
  5. customThe filter cake was dried
  6. addition10 mL of a solvent mixture of dichloromethane/methanol (V:V=50:1)
  7. additionwas added
  8. additionUpon completion of the addition
  9. filtrationThen the mixture was filtered
  10. washthe filter cake was washed with dichloromethane (2 mL×3)
  11. customdried

Sources & evidence

ORD record
ord-ba5e1af5bb1148b69472bf70bd4a01a6
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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