Aluminum(III) Chloride → HCID 12649786, compound

HRID 917989Notes

Reaction equation

HRID 917989 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[F:11][C:12]1[CH:20]=[CH:19][C:18]2[N:17]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:16]3[CH2:28][N:29]([C:31](OCC)=O)[CH2:30][C:15]=3[C:14]=2[CH:13]=1>O1CCCC1>[F:11][C:12]1[CH:20]=[CH:19][C:18]2[N:17]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[C:16]3[CH2:28][N:29]([CH3:31])[CH2:30][C:15]=3[C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 12649781HCID 12649781, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12649786HCID 12649786, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 244 mg. (6.4 m moles) of lithium aluminum hydride in 20 ml. of dry tetrahydrofuran under a nitrogen atmosphere and cooled to -10° C. is added 284 mg. (2.1 m moles) of aluminum chloride and the resulting reaction mixture allowed to stir for 30 min. 7-Fluoro-4-(p-fluorophenyl)-2-carbethoxy1,2,3,4-tetrahydropyrrolo[3,4-b]indole (2.9 m moles) in 10 ml. of the same solvent is added dropwise to the cold solution with stirring. After one hour, the reaction is quenched with 5 ml. of water added dropwise, and the mixture allowed to warm to room temperature. The mixture is filtered and the solids washed with hot tetrahydrofuran. The combined filtrate and washings are concentrated to a brown solid, which on dissolution in diethyl ether followed by treatment with ether saturated with hydrogen chloride provides 448 mg. of the desired product, m.p. 160°-165° C.

Workup

  1. additionTo a mixture of 244 mg
  2. additionis added 284 mg
  3. additionof the same solvent is added dropwise to the cold solution
  4. stirringwith stirring
  5. waitAfter one hour
  6. customthe reaction is quenched with 5 ml
  7. additionof water added dropwise
  8. filtrationThe mixture is filtered
  9. washthe solids washed with hot tetrahydrofuran
  10. concentrationThe combined filtrate and washings are concentrated to a brown solid, which on dissolution in diethyl ether
  11. customprovides 448 mg

Sources & evidence

ORD record
ord-56752751eb6f4a65a339df45351b6ed6
Source dataset
uspto-grants-1976_07
Patent number
US03968231

Reaction notes

Loading…