4-Bromophenylhydrazine hydrochloride → HCID 12050050, compound

HRID 2228635Notes

Reaction equation

HRID 2228635 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[CH2:11]([CH:13]([CH2:17][CH3:18])[C:14](=O)[CH3:15])[CH3:12]>>[Br:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][CH:11]([CH3:12])[C:13]2([CH2:17][CH3:18])[CH2:14][CH3:15]

Participants

3

Reactant 2

HCID 121574-Bromophenylhydrazine hydrochlorideHCID 802242-Pentanone, 3-ethyl-

Product 1

HCID 12050050HCID 12050050, compoundYield 65%

Procedure

This compound was prepared according to the procedure for Example 1 using 4-bromo-phenyl hydrazine hydrochloride (5.9 g, 26.3 mmol) and 3-ethyl-2-pentanone (3.0 g, 26.3 mmol). The subtitled compound (4.5 g) was obtained in 65% yield as a yellowish oil: 1H-NMR (CDCl3) δ0.81 (t, J=7.4 Hz, 3H), 0.83 (t, J=7.4 Hz, 3H), 1.18 (d, J=6.5 Hz, 3H), 1.42 (dq, J=14.0, 7.4 Hz, 1H), 1.66 (dq, J=14.0, 7.4 Hz, 3H), 3.73 (q, J=6.5 Hz, 1H), 6.47 (d, J=8.2 Hz, 1H), 7.02 (d, J=2 Hz, 1H), 7.09 (dd, J=8.2, 2.0Hz, 1H); 13C-NMR (CDCl3) δ10.46, 10.66, 17.70 (q), 26.5, 29.67 (t), 52.25 (s), 64.80 (d), 111.64 (s), 112.41, 129.07, 131.58 (d), 139.57, 151.04 (s); MS (EI) m/z 268, 270 (M+H)+.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b458d4a225384186b1c218be2a2db902
Source dataset
uspto-grants-2002_07
Patent number
US06417214B1

Reaction notes

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