Cyanogen Bromide → HCID 23467856, compound

HRID 1389138Notes

Reaction equation

HRID 1389138 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH:10]3[CH2:19][CH2:18][CH2:17][CH:16]4[C:11]3([CH2:12][CH2:13][N:14](C)[CH2:15]4)[C:7]=2[CH:6]=[CH:5][CH:4]=1.N#CBr.[OH-].[K+]>C(Cl)Cl.C(O)CO>[CH3:1][O:2][C:3]1[C:8]2[O:9][CH:10]3[CH2:19][CH2:18][CH2:17][CH:16]4[C:11]3([CH2:12][CH2:13][NH:14][CH2:15]4)[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 14797Potassium HydroxideHCID 13193920HCID 13193920, compound

Product 1

HCID 23467856HCID 23467856, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 6344DichloromethaneSolvent

Procedure

Thus, 9-methoxy-3-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-benzo[4,5]furo[3,2-e]isoquinoline (Example 2d) is heated to reflux with cyanogen bromide in methylene chloride and the crude product is then heated with potassium hydroxide in ethylene glycol to 170° to give 9-methoxy-2,3,4,4a,5,6,7,7a-octahydro-1H-benzo[4,5]furo[3,2-e]isoquinoline (R1 =H; R2 =OMe; R3, R4, R5 =H).

Sources & evidence

ORD record
ord-f2975eb5587b4b52b015e7fc56324722
Source dataset
uspto-grants-1981_01
Patent number
US04243668

Reaction notes

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