Sodium Hydroxide → 5,6-Dimethoxy-2-methyl-2,3-dihydro-1H-isoindole--hydrogen chloride (1/1)

HRID 704451Notes

Reaction equation

HRID 704451 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[C:9]([CH2:10][NH:11][CH3:12])=[CH:8][C:7]([O:13][CH3:14])=[C:6]([O:15][CH3:16])[CH:5]=1.[OH-].[Na+]>[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.C1C=CC=CC=1>[ClH:2].[CH3:16][O:15][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][C:7]=1[O:13][CH3:14])[CH2:10][N:11]([CH3:12])[CH2:3]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20074345HCID 20074345, compound

Product 1

HCID 200743475,6-Dimethoxy-2-methyl-2,3-dihydro-1H-isoindole--hydrogen chloride (1/1)Yield 7.8%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 241BenzeneSolvent

Procedure

23 g (0.1 mol) of N-(6-chloromethyl-3,4-dimethoxybenzyl)-methylamine hydrochloride was added at a temperature of from 15° to 18° C. to a suspension comprising 50 ml of a 50% sodium hydroxide aqueous solution, 230 ml of benzene and 1 ml of a 90% trioctylmethylammonium chloride aqueous solution over a period of 2 minutes. The mixture was stirred for 3 hours, and then the organic layer of the reaction solution was separated, washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and 50 ml of 6N hydrochloric acid was added to the residue. The mixture was again evaporated under reduced pressure to dryness. The crystalline residue was washed with ethanol to obtain 12.65 g (yield: 51.2%) of the above identified compound. From the filtrate, 1.8 g (yield: 7.8%) of secondary crystals were obtained. The total amount was 14.4 g (total yield: 63.1%). Melting point: 227° C. (decomposed)

Workup

  1. customof 2 minutes
  2. customthe organic layer of the reaction solution was separated
  3. washwashed with water
  4. dry with materiala saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure, and 50 ml of 6N hydrochloric acid
  6. additionwas added to the residue
  7. customThe mixture was again evaporated under reduced pressure to dryness
  8. washThe crystalline residue was washed with ethanol
  9. customto obtain 12.65 g (yield: 51.2%) of the

Sources & evidence

ORD record
ord-aeaecf71afd441beb77e8abdd12b6875
Source dataset
uspto-grants-1991_01
Patent number
US04987235

Reaction notes

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