Acetic Acid → 1-Acetyl-5-carbomethoxy-7-chloro-4-methoxy-1,2-dihydroindole

HRID 2074002Notes

Reaction equation

HRID 2074002 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([O:18][CH3:19])[C:9]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][C:11]=2[Cl:13])[CH:6]=[CH:5]1)(=[O:3])[CH3:2].C(O)(=O)C>[Pt].CO>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([O:18][CH3:19])[C:9]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][C:11]=2[Cl:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 104931031-Acetyl-5-carbomethoxy-7-chloro-4-methoxyindole

Product 1

HCID 105649501-Acetyl-5-carbomethoxy-7-chloro-4-methoxy-1,2-dihydroindole

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

The mixture of the indole of step 8 above (0.9 g) and Pt-C (0.2 g), acetic acid and MeOH (100 ml) is stirred under H2 at 1 atm. pressure for 48 hours. The catalyst is filtered (celite), the filtered material is washed (MeOH) and the reaction mixture and methanol washings are evaporated. The residue is diluted with CH2Cl2, washed with saturated NaHCO3, dried (MgSO4) and evaporated affording a colorless, semicrystalline material which is determined to be the desired compound by NMR. M.P. 107°-109° C.

Workup

  1. filtrationThe catalyst is filtered (celite)
  2. washthe filtered material is washed (MeOH)
  3. customthe reaction mixture and methanol washings are evaporated
  4. additionThe residue is diluted with CH2Cl2
  5. washwashed with saturated NaHCO3
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customaffording a colorless, semicrystalline material which

Sources & evidence

ORD record
ord-be1d126f7a2a4da2bef77007ed389b1e
Source dataset
uspto-grants-1990_04
Patent number
US04920219

Reaction notes

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