N-dodecyl-4-nitrobenzamide → HCID 22767596, compound

HRID 735853Notes

Reaction equation

HRID 735853 reaction equation
[CH2:1]([NH:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H][H]>>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([NH:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:24])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 4271901N-dodecyl-4-nitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 22767596HCID 22767596, compoundYield 98%

Procedure

The same procedure as employed in the preparation of Example 1 (step c) using N-dodecyl-4-nitrobenzamide and hydrogen at a pressure of 20 bar at 50° C. gave the title compound (98%). 1H NMR (DMSO-d6, 300 MHz) δ 7.93 (t, 1H, J=5.6 Hz), 7.53 (d, 2H, J=8.7 Hz), 6.50 (d, 2H, J=8.7 Hz), 8.30 (s, 2H), 3.16 (m, 2H), 1.36-1.52 (m, 2H), 1.12-1.33 (m, 18H), 0.83 (t, 3H, J=6.7 Hz). HPLC (Condition A), Rt: 4.87 min (HPLC purity 99.7%).

Workup

  1. customThe same procedure as employed in the preparation of Example 1 (step c)
  2. customat 50° C.

Sources & evidence

ORD record
ord-f22e89cbbc494034ac85bb3193750319
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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