Hydrochloric Acid → 5-Methoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 546286Notes

Reaction equation

HRID 546286 reaction equation
O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(NC(=O)[O-])C.[CH3:18][O:19][C:20]1[C:21]([Cl:33])=[CH:22][C:23]2[CH:24]([CH3:32])[CH:25]3[CH2:29][NH:28][CH2:27][CH:26]3[C:30]=2[CH:31]=1.Cl>CO>[CH3:18][O:19][C:20]1[C:21]([Cl:33])=[CH:22][C:23]2[CH:24]([CH3:32])[CH:25]3[CH2:29][NH:28][CH2:27][CH:26]3[C:30]=2[CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 17749109Barium hydroxide, octahydrateHCID 86602844N-Ethylcarbamate 5-methoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 117085025-Methoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Barium hydroxide octahydrate (0.63 g, 2.0 mmol) was added to a solution of N-ethylcarbamate-5-methoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (61 mg, 0.2 mmol) in MeOH (4 mL), and stirred for 24 hours at reflux. The reaction mixture was cooled to room temperature and neutralized to pH=7 with aqueous HCl (50 mL, 1 M). The product was extracted with CH2Cl2, dried over MgSO4, and concentrated. The crude product was purified by reverse-phase liquid chromatography to afford the title compound. MS calculated for C13H16ClNO+H: 238, observed: 238.

Workup

  1. temperatureat reflux
  2. extractionThe product was extracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by reverse-phase liquid chromatography

Sources & evidence

ORD record
ord-f67e289efa8b419a9fde051960bd9042
Source dataset
uspto-grants-2011_05
Patent number
US07935830B2

Reaction notes

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