Triethyloxonium tetrafluoroborate → 5-Ethoxy-1,3-dihydropyrrolo[4,3,2-de]isoquinoline

HRID 1284029Notes

Reaction equation

HRID 1284029 reaction equation
[NH:1]1[C:11]2[C:12]3[C:3]([CH2:4][NH:5][C:6](=[O:13])[C:7]=3[CH:8]=[CH:9][CH:10]=2)=[CH:2]1.F[B-](F)(F)F.[CH2:19]([O+](CC)CC)[CH3:20]>C(Cl)Cl>[CH2:19]([O:13][C:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[NH:1][CH:2]=[C:3]([C:12]=23)[CH2:4][N:5]=1)[CH3:20]

Participants

4

Reactant 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 3041095Pyrrolo(4,3,2-de)isoquinolin-5(1H)-one, 3,4-dihydro-

Product 1

HCID 215155225-Ethoxy-1,3-dihydropyrrolo[4,3,2-de]isoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,4-Dihydropyrrolo[4,3,2-de]isoquinolin-5(lH)-one (8.6 g), described in Example 4, is added in one portion to a solution of 12 g of triethyloxonium fluoroborate [H.-L. Pan and T. L. Fletcher, J. Org. Chem., 27, 3639 (1962)] in 500 ml dry methylene chloride. The suspension is stirred for 24 hours. The solid is collected and washed with a little methylene chloride and then ether to give 5-ethoxy-1,3-dihydropyrrolo[4,3,2-de]isoquinoline hydrofluoroborate, mp 233° - 234°C, νmaxnujol 3380, 3280, 1645, 1605, 1594, 1540 and 1512 cm-1.

Workup

  1. customThe solid is collected
  2. washwashed with a little methylene chloride

Sources & evidence

ORD record
ord-e231ae5f85aa437d8a279ee285f23c8f
Source dataset
uspto-grants-1976_08
Patent number
US03978066

Reaction notes

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