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

HRID 2074003Notes

Reaction equation

HRID 2074003 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([O:18][CH3:19])[C:9]([C:14]([O:16]C)=[O:15])=[CH:10][C:11]=2[Cl:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>[OH-].[Na+].CO>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([O:18][CH3:19])[C:9]([C:14]([OH:16])=[O:15])=[CH:10][C:11]=2[Cl:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

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

Product 1

HCID 148832261-Acetyl-5-carboxy-7-chloro-4-methoxy-1,2-dihydroindole

Reagents, catalysts & solvents 1

HCID 23721981Sodium hydroxide methanolSolvent

Procedure

A mixture of the indole ester of step 9 above (0.8 g) and 10% aqueous NaOH/MeOH (20 ml/80 ml) is stirred under reflux for 2 hours. The reaction mixture is concentrated and the aqueous residue is diluted with water and extracted with CHCl3. The organic layer is dried (MgSO4) and evaporated affording an off-white solid which is determined to be the desired compound by NMR.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationThe reaction mixture is concentrated
  3. additionthe aqueous residue is diluted with water
  4. extractionextracted with CHCl3
  5. dry with materialThe organic layer is dried (MgSO4)
  6. customevaporated
  7. customaffording an off-white solid which

Sources & evidence

ORD record
ord-2d6adf4bd802410b97733c9b3797b538
Source dataset
uspto-grants-1990_04
Patent number
US04920219

Reaction notes

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