Morpholine → 2-Benzamido-4-chloro-5-[2-(p-aminophenoxy]-myristamido]-phenol

HRID 620705Notes

Reaction equation

HRID 620705 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([NH:17][C:18](=[O:42])[CH:19]([O:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-])=O)=[CH:35][CH:34]=2)[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][C:11]=1[OH:43])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCOCC1.[H][H]>[Ni].O1CCCC1>[C:1]([NH:9][C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([NH:17][C:18](=[O:42])[CH:19]([O:32][C:33]2[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=2)[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][C:11]=1[OH:43])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 141224212-Benzamido-4-chloro-5-[2-(p-nitrophenoxy]-myristamido]-phenolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 141224222-Benzamido-4-chloro-5-[2-(p-aminophenoxy]-myristamido]-phenol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

An amount of 670 g (1.10 mol) of 2-benzamido-4-chloro-5-[2-(p-nitrophenoxy]-myristamido]-phenol in the presence of 2370 ml of tetrahydrofuran, 47.8 g of morpholine, and 22 ml of Raney nickel is reduced in an autoclave at an initial hydrogen pressure of 10 MPa and a temperature of 40° C. After 90 min the theoretical amount of hydrogen is found to be taken up. The catalyst is filtered off. The filtrate is concentrated by evaporation to a volume of 1 l and then poured out in 4 l of ethanol. The precipitate is filtered off and dried.

Workup

  1. customa temperature of 40° C
  2. filtrationThe catalyst is filtered off
  3. concentrationThe filtrate is concentrated by evaporation to a volume of 1 l
  4. additionpoured out in 4 l of ethanol
  5. filtrationThe precipitate is filtered off
  6. customdried

Sources & evidence

ORD record
ord-0206dc79aeec4df7b81c62b21cea761d
Source dataset
uspto-grants-1989_04
Patent number
US04822729

Reaction notes

Loading…