3-Nitro-5-(octadecyloxy)benzamide → HCID 19389096, compound

HRID 1110263Notes

Reaction equation

HRID 1110263 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:12]=1)[C:7]([NH2:9])=[O:8])([O-])=O.[H][H]>[Pd].C1COCC1>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:12]=1)[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 2

HCID 193889283-Nitro-5-(octadecyloxy)benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 19389096HCID 19389096, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4.75 g of 3-nitro-5-(octadecyloxy)benzamide and 1.0 g of 10% palladium on carbon in 750 ml of THF was shaken in a hydrogen atmosphere at room temperature until uptake ceased after 4 hours. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure to a solid which was recrystallized from methanol to give 4.0 g (91% yield, mp 139°-143°) of 3-amino-5-(octadecyloxy)benzamide.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated at reduced pressure to a solid which
  3. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-2e7078492c214bdc89972f8c91ca2a52
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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