Ethyl 6-benzyloxy-4-chloro-1-methyl-2-indolecarboxylate → Ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate

HRID 1067782Notes

Reaction equation

HRID 1067782 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:15]2[CH3:18])=[C:11]([Cl:24])[CH:10]=1)C1C=CC=CC=1>O1CCCC1.[Pd]>[Cl:24][C:11]1[CH:10]=[C:9]([OH:8])[CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:15]2[CH3:18]

Participants

4

Reactant 1

HCID 21194606Ethyl 6-benzyloxy-4-chloro-1-methyl-2-indolecarboxylate

Product 1

HCID 21194263Ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylateYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In 60 ml of tetrahydrofuran was dissolved 2.20 g (6.40 mmol) of ethyl 6-benzyloxy-4-chloro-1-methyl-2-indolecarboxylate. After 0.3 g of 10% palladium/carbon was added to the solution, catalytic hydrogenation was performed at ambient temperature under normal pressure. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 1.50 g (92.4%) of ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate. 1H NMR (CDCl3) δ: 1.38-1.44 (3H, m), 3.98 (3H, s), 4.33-4.40 (2H, m), 5.07 (1H, s), 6.67 (1H, t, J=0.99 Hz), 6.78 (1H, d, J=1.98 Hz), 7.30 (1H, d, J=0.99 Hz)

Workup

  1. customwas performed at ambient temperature under normal pressure
  2. customAfter completion of the reaction
  3. filtrationthe catalyst was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5a7a4fdf663c4506afd8a480facaae20
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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