Water → methyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate

HRID 1871042Notes

Reaction equation

HRID 1871042 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[NH:7][C:8]2[C:13]([C:14]=1[C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:11]=[CH:10][CH:9]=2.[OH-].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:18][O:17][C:15]([C:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]2[CH2:2][CH2:3][CH2:4][O:5][C:6]=12)=[O:16]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 9816818Methyl 2-(3-chloropropoxy)indole-3-carboxylate

Product 1

HCID 11746477methyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of methyl 2-(3-chloropropoxy)-indole-3-carboxylate (81.5 g, 0.304 mole), aqueous sodium hydroxide solution (3 ml, 10.8M, 0.335 mole), water (31 ml) and tetrabutylammonium bromide (4.9 g, 0.015 mole) in toluene (815 ml ) was stirred at 50-60° C. for about 45 minutes. The aqueous layer was removed and the organic layer washed twice with water (100 ml each wash). The resulting toluene solution was dried by azeotropic distillation of solvent (265 ml ) under reduced pressure (60° C., 160 mbar) giving a dried solution of the title compound in toluene.

Workup

  1. customThe aqueous layer was removed
  2. washthe organic layer washed twice with water (100 ml each wash)
  3. dry with materialThe resulting toluene solution was dried by azeotropic distillation of solvent (265 ml ) under reduced pressure (60° C., 160 mbar)

Sources & evidence

ORD record
ord-f4f6b3b70f9c4aefa378c3a94ae9d679
Source dataset
uspto-grants-2000_08
Patent number
US06100397

Reaction notes

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