Tetrahydrofuran → 5(-4-Aminophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

HRID 2166363Notes

Reaction equation

HRID 2166363 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].O1CCCC1>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 138000585-(4-Nitrophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

Product 1

HCID 138000665(-4-Aminophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

15 g of 5-(4-nitrophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester is hydrogenated in 450 ml of methanol: tetrahydrofuran=1:1 with 7.5 g of palladium on carbon (10%) at room temperature under hydrogen normal pressure. After filtering and concentrating, it is recrystallized from ethanol and 10.8 g (77% of theory) of 5-(4-aminophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester of a melting point of 222°-224° C. is obtained.

Workup

  1. customat room temperature
  2. filtrationAfter filtering
  3. concentrationconcentrating
  4. customit is recrystallized from ethanol and 10.8 g (77% of theory) of 5-(4-aminophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester of a melting point of 222°-224° C.
  5. customis obtained

Sources & evidence

ORD record
ord-38eb7e7c835c492295865c48e196f6c9
Source dataset
uspto-grants-1990_07
Patent number
US04945090

Reaction notes

Loading…