Dimethyl ether ethylene glycol → 4-Hydroxy-2-carbamoyl-6-methyl indole

HRID 903924Notes

Reaction equation

HRID 903924 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19](=[O:21])[NH2:20])[NH:13]2)C1C=CC=CC=1.C(O)CO.COC.[H][H]>[Pd].CO>[OH:8][C:9]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19](=[O:21])[NH2:20])[NH:13]2

Participants

6

Reactant 3

HCID 21863332Dimethyl ether ethylene glycolHCID 233355554-Benzyloxy-2-carbamoyl-6-methyl indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 233355454-Hydroxy-2-carbamoyl-6-methyl indoleYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8.5 g of the thus obtained 4-benzyloxy-2-carbamoyl-6-methyl indole are hydrogenated in a composition of 100 ml methanol and 50 ml ethylene glycol-dimethyl ether during addition of 1.0 g 10% Pd/C up to the absorption of the theoretical amount of hydrogen. The catalyst is aspirated and the filtrate is evaporated in vacuum. There is obtained 5.4 (~93% of theory) 4-hydroxy-2-carbamoyl-6-methyl indole as a light yellow syrup.

Workup

  1. customthe filtrate is evaporated in vacuum

Sources & evidence

ORD record
ord-d99d1b05acac4a8d8cbd0664b21e16b1
Source dataset
uspto-grants-1980_10
Patent number
US04229464

Reaction notes

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