Methyl iodide → HCID 13472775, compound

HRID 1248180Notes

Reaction equation

HRID 1248180 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:21][CH3:22])=[C:5]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[CH:7]3[CH2:8][N:9]=[CH:10][C:11]([CH:12]=1)=[C:6]23.C[I:24].[CH2:25]([Mg]Br)C.C1C2C(=CC=CC=2)C=CN=1>>[I-:24].[CH3:1][O:2][C:3]1[C:4]([O:21][CH3:22])=[C:5]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[CH:7]3[CH2:8][N+:9]([CH3:25])=[CH:10][C:11]([CH:12]=1)=[C:6]23

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 8405IsoquinolineHCID 13472769HCID 13472769, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 13472775HCID 13472775, compound

Procedure

By following serially the procedure of step (a) of example 5 and the procedure of example 6, and selecting 5,6-dimethoxy-1,7,8,12b-tetrahydrobenzo[6,7]cyclohepta[1,2,3-de]isoquinoline (described in example 2) as the starting material of formula II, methyl iodide as the organohalide and ethyl magnesium bromide as the Grignard reagent, (3,12b-trans)-3-ethyl-5,6-dimethoxy-2-methyl-1,2,3,7,8,12b-hexahydrobenzo[6,7]cyclohepta]1,2,3-de]isoquinoline, mp 92°-94° C., was obtained via 5,6-dimethoxy-2-methyl-1,7,8,12b-tetrahydrobenzo[6,7]cyclohepta[1,2,3-de]-isoquinolinium iodide, mp 195°-210° C., NMR (DMSO-d6) δ 3.83 (s, 3H), 3.88 (s, 3H), 3.97 (s, 3H), 4.42 (m, 2H), 5.18 (m, 1H), 7.10 (m, 4H), 7.38 (s, 1H), 9.17 (s, 1H).

Sources & evidence

ORD record
ord-c969943f6da14e0ab514d4a0b75b81b6
Source dataset
uspto-grants-1985_06
Patent number
US04522946

Reaction notes

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