Phenol → n-Benzyl-1-methyl-4-nitro-3-phenoxy-1h-pyrazol-5-amine

HRID 2262326Notes

Reaction equation

HRID 2262326 reaction equation
[CH2:1]([NH:8][C:9]1[N:10]([CH2:18]CC)[N:11]=[C:12](Br)[C:13]=1[N+:14]([O-:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([OH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-]>CN1CCCC1=O.[Cu]I>[CH2:1]([NH:8][C:9]1[N:10]([CH3:18])[N:11]=[C:12]([O:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]=1[N+:14]([O-:16])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 19660Carbonate IonHCID 13007229benzyl(5-bromo-4-nitro-2-propyl-2H-pyrazol-3-yl)amine

Product 1

HCID 57957914n-Benzyl-1-methyl-4-nitro-3-phenoxy-1h-pyrazol-5-amine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Treatment of 3,5-dibromo-4-nitro-1H-pyrazole 1 with MeI and NaH in DMF affords 3,5-dibromo-1-methyl-4-nitro-1H-pyrazole 2. Nucleophilic aromatic substitution of the compound 2 with benzylamine in DMSO produces benzyl-(5-bromo-2-methyl-4-nitro-2H-pyrazol-3-yl)-amine 3. Treatment of the compound 3 with phenol in the presence of copper (I) iodide and cecium carbonate in N-methylpyrrolidinone (NMP) under microwave irradiation provides N-benzyl-1-methyl-4-nitro-3-phenoxy-1H-pyrazol-5-amine 4 (Tetrahedron Lett, 2003, 44, 3445). Hydrogenation of the compound 4 with Pd/C at 60 psi hydrogen in ethanol affords 1-methyl-3-phenoxy-1H-pyrazole-4,5-diamine 5. II. Keratin Dyeing Composition Components

Sources & evidence

ORD record
ord-c202959e29b74a5aa414af910efce754
Source dataset
uspto-grants-2010_12
Patent number
US07850742B2

Reaction notes

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