Aniline → HCID 23139493, compound

HRID 540508Notes

Reaction equation

HRID 540508 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH3:19])[C:6]=1[C:7]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:8]=1[O:16][CH2:17][CH3:18].C(OC1C=CC([N+]([O-])=O)=CC=1C1N(C)N=CC=1)C.C1C(=O)N(Br)C(=O)C1.NC1C=CC=CC=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH3:19])[C:6]=1[C:7]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:8]=1[O:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 6115AnilineHCID 67184N-bromobutanimideHCID 23139459HCID 23139459, compoundHCID 23139490HCID 23139490, compound2×

Product 1

HCID 23139493HCID 23139493, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-5-(2-ethoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole: The crude reaction mixture of 5-(2-ethoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole was treated with NBS in DMF, in a similar manner as described in Example 1.1, Step D, provided brominated compound 4-bromo-5-(2-ethoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole. It was reduced directly to the aniline as described in this example above. LCMS m/z (%)=326 (M+H79Br, 88), 328 (M+H81Br, 100). 1H NMR (400 MHz, CDCl3) δ: 8.38 (dd, J=2.7, 9.2 Hz, 1H), 8.22 (d, J=2.7 Hz, 1H), 7.59 (s, 1H), 7.11 (d, J=9.2 Hz, 1H), 4.14-4.32 (m, 2H), 3.76 (s, 3H), 1.43 (t, J=6.8 Hz, 3H).

Workup

  1. customprovided

Sources & evidence

ORD record
ord-2cf3481c687c4c3297bda163da3e1342
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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