Acetic Acid → HCID 178433881, compound

HRID 59613Notes

Reaction equation

HRID 59613 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[N:15][NH:16][C:17]3[C:18]([O:32]C)=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([OH:31])=[O:30])[CH:24]=4)[CH:20]=[CH:21][CH:22]=3)[C:11]([CH3:34])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(O)(=O)C>Br>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[N:15][NH:16][C:17]3[C:18]([OH:32])=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([OH:31])=[O:30])[CH:24]=4)[CH:20]=[CH:21][CH:22]=3)[C:11]([CH3:34])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 178493807HCID 178493807, compound

Product 1

HCID 178433881HCID 178433881, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 3′-{N′-[1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]hydrazino}-2′-methoxybiphenyl-3-carboxylic acid (4 g), prepared as in Example 3, in 48% aqueous hydrobromic acid (35 mL) and glacial acetic acid (35 mL) was stirred and heated under reflux for about 60 hours. The reaction mixture was concentrated under vacuum to a thick residue. Water (40 mL) was added and basified to pH 7-8 using saturated solution of sodium bicarbonate (20 mL). The mixture was filtered to give an orange solid, which was washed with water (25 mL) and dried in an oven at 55° C. about to about 60° C. for about 12 hours.

Workup

  1. temperatureheated
  2. temperatureunder reflux for about 60 hours
  3. concentrationThe reaction mixture was concentrated under vacuum to a thick residue
  4. additionWater (40 mL) was added
  5. filtrationThe mixture was filtered
  6. customto give an orange solid, which
  7. washwas washed with water (25 mL)
  8. customdried in an oven at 55° C. about to about 60° C. for about 12 hours

Sources & evidence

ORD record
ord-57bd62c997a348619108250ef8d27e57
Source dataset
uspto-grants-2016_09
Patent number
US09440927B2

Reaction notes

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