4-Nitro-benzoic acid 1-hexyl-11-(4-nitro-phenoxy carbonyl)-undec-3-enyl ester → HCID 131735513, compound

HRID 522191Notes

Reaction equation

[CH2:1]([CH:7]([O:30][C:31](=[O:41])[C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-])=O)=[CH:34][CH:33]=1)[CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>C(OCC)(=O)C.[Ni]>[NH2:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH:7]([O:30][C:31](=[O:41])[C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[O:19])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 62.5 °C

Procedure

To a solution of 4-nitro-benzoic acid 1-hexyl-11-(4-nitro-phenoxy carbonyl)-undec-3-enyl ester (300 g) in ethyl acetate (1.5 L) in a pressure vessel was added Raney Nickel (120 g) added, and the mixture stirred under an atmosphere of Hydrogen (8-10 Kg) for 8 hours at a temperature of 60-65° C. The catalyst was removed by filtration. The solvent was distilled off completely under reduced pressure at 65-70° C. and removed traces for 1 hour at 85-90° C. to get pure 4-aminobenzoic acid 11-(4-amino-phenoxycarbonyl)-1-hexyl-undec-3-enyl ester product as deep yellow thick syrup (190 g). The resulting compound was characterized by 1H NMR (CDCl3) δ 0.88 (t, 3H, CH3), 1.2-1.65 (m, 24H, 12×CH2), 2.12 (t, 2H, COCH2), 3.5 (m, 1H, CH) 5.12 (m, 1H, CH), 5.45 (m, 1H, CH), 6.55 (m, 4H, Ar), 6.85 (m, 2H, Ar), 7.75 (m, 2H, Ar).

Workup

additionadded
customThe catalyst was removed by filtration
distillationThe solvent was distilled off completely under reduced pressure at 65-70° C.
customremoved traces for 1 hour at 85-90° C.

Sources & evidence

ORD record: ord-82157e7f623d4c238fd369a736ff39f7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328192B2

Reaction notes

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