4-Aminophenol → HCID 72734373, compound

HRID 870413Notes

Reaction equation

HRID 870413 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][N:10]1[C:14]([CH3:15])=[C:13]([C:16]([OH:18])=O)[C:12](=[O:19])[N:11]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC[N:28]=[C:29]=[N:30][CH2:31][CH2:32][CH2:33]N(C)C.C1C=NC2N(O)N=NC=2C=1.[CH2:47](Cl)[Cl:48]>CCOC(C)=O.O>[NH2:28][C:29]1[C:47]([Cl:48])=[C:33]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:16]([C:13]3[C:12](=[O:19])[N:11]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:10]([CH3:9])[C:14]=3[CH3:15])=[O:18])=[CH:3][CH:4]=2)[CH:32]=[CH:31][N:30]=1

Participants

8

Reactant 5

HCID 4034-AminophenolHCID 6344DichloromethaneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 246564Antipyric acid

Product 1

HCID 72734373HCID 72734373, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
46 °C

Procedure

To a mixture of 4-aminophenol (1.09 g, 10 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (2.37 g, 10.2 mmol) in DCM (30 mL) was added EDCI (2.3 g, 12 mmol) and HOAT (0.27 g, 2 mmol). The mixture was stirred at 46° C. for 4 hours, then cooled to rt and diluted with EtOAc (10 mL) and water (10 mL). The mixture was stirred at rt for 1 hour, then filtered to give the title compound as a white solid (1.7 g, 52.5%).

Workup

  1. temperaturecooled to rt
  2. stirringThe mixture was stirred at rt for 1 hour
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ad0a1bfc90334993a3a11a249387bfbb
Source dataset
uspto-grants-2015_03
Patent number
US08969388B1

Reaction notes

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