Ammonia → 4-Benzyloxy-2-carbamoyl-6-methyl indole

HRID 903923Notes

Reaction equation

HRID 903923 reaction equation
[CH2:1]([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]CC)=O)[NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:24]>CO>[CH2:1]([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])[NH2:24])[NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 23335518Ethyl 4-(benzyloxy)-6-methyl-1H-indole-2-carboxylate

Product 1

HCID 233355554-Benzyloxy-2-carbamoyl-6-methyl indoleYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20.0 g 4-benzyloxy-2-ethoxycarbonyl-6-methyl indole (see preparation of the primary products in connection with Example 1) are heated together with 200 ml each of methanol and liquid ammonia in the autoclave for 16 hours, to 100° C. The solution is evaporated and the residue is chromatographed on silica gel (fluxing agent: chloroform/methanol 98:2). There is obtained 8.5 g (~46% of theory) 4-benzyloxy-2-carbamoyl-6-methyl indole; m.p. 185°-187° C.

Workup

  1. custompreparation of the primary products in connection with Example 1)
  2. customThe solution is evaporated
  3. customthe residue is chromatographed on silica gel (fluxing agent: chloroform/methanol 98:2)

Sources & evidence

ORD record
ord-bf0eb90eac3a4c789bc499fa9de57ff3
Source dataset
uspto-grants-1980_10
Patent number
US04229464

Reaction notes

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