Hydrochloric Acid → HCID 178433872, compound

HRID 1814205Notes

Reaction equation

HRID 1814205 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12]([CH:15]=O)=[C:11]([CH3:17])[NH:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].Cl.[NH2:19][C:20]1[C:21]([OH:35])=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([OH:34])=[O:33])[CH:27]=2)[CH:23]=[CH:24][CH:25]=1.C([O-])(=O)C.[Na+].Cl>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[CH:15][NH:19][C:20]3[C:21]([OH:35])=[C:22]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([OH:34])=[O:33])[CH:27]=4)[CH:23]=[CH:24][CH:25]=3)[C:11]([CH3:17])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 7591261-(3,4-dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazole-4-carbaldehydeHCID 69220589(1,1'-Biphenyl)-3-carboxylic acid, 3'-amino-2'-hydroxy-, hydrochloride (1:1)

Product 1

HCID 178433872HCID 178433872, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(3,4-dimethylphenyl)-3-methyl-5-oxo-3-pyrazolin-4-carbaldehyde (10 mg, 0.043 mmol) and 3′-amino-2′-hydroxybiphenyl-3-carboxylic acid hydrochloride (11 mg, 0.042 mmol) in ethanol (1 mL) was shaken with 0.2M aq. sodium acetate (0.25 mL, 0.05 mmol) for 1 h. 0.06M aq. hydrochloric acid (3 mL) was added and shaking continued for 1 h. The solid was filtered, washed with water and dried under reduced pressure to afford the title compound (14 mg, 74%) as a cream-coloured powder. 1H NMR (300 MHz, d6-DMSO) δ 13.08 (br s, 1H), 11.79 (d, J=13.8 Hz, 1H), 9.56 (s, 1H), 8.71 (d, J=13.2 Hz, 1H), 8.14 (s, 1H), 7.97 (d, J=7.8 Hz, 1H), 7.83-7.80 (m, 3H), 7.71 (d, J=8.2 Hz, 1H), 7.62 (t, J=7.8 Hz, 1H), 7.16-7.11 (m, 3H), 2.31 (s, 3H), 2.26 (s,3H), 2.22 (s, 3H).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-1d53dd4bbd9b4237815c34f923b83f3a
Source dataset
uspto-grants-2005_04
Patent number
US06875786B2

Reaction notes

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