Ethanol → HCID 23139493, compound

HRID 540507Notes

Reaction equation

HRID 540507 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].O.O.Cl[Sn]Cl.CCO>>[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

4

Reactant 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 23139490HCID 23139490, compound

Product 1

HCID 23139493HCID 23139493, compound

Procedure

3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-ethoxy-phenylamine was prepared in a similar manner as described in Example 1.1 using 4-bromo-5-(2-ethoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole, SnCl2.2H2O in EtOH [0.225 g, 0.76 mmol, 81% for three steps from 2-(2-methyl-2H-pyrazol-3-yl)-4-nitro-phenol]. LCMS m/z (%)=296 (M+H79Br, 100), 298 (M+H81Br, 98). 1H NMR (400 MHz, CDCl3) δ: 7.52 (s, 1H), 6.86 (d, J=8.7 Hz, 1H), 6.77 (dd, J=2.2, 8.5 Hz, 1H), 6.62 (d, J=2.3 Hz, 1H), 3.82-4.00 (m, 2H), 3.73 (s, 3H), 3.24-3.58 (broad s, 2H), 1.24 (t, J=6.8 Hz, 3H).

Sources & evidence

ORD record
ord-68b038651edb418594caf4c2c8e08387
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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