3-Cyclohexene-1-carboxylic acid → HCID 20195502, compound

HRID 370486Notes

Reaction equation

HRID 370486 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]=2Br)=[CH:5][CH:4]=1.[N+:19]([O-:24])([N+]([O-])=O)=[O:20].C1CCC(C(O)=O)CC=1>C(O)(=O)C>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]=2[N+:19]([O-:24])=[O:20])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 209033-Cyclohexene-1-carboxylic acidHCID 25352Nitrogen oxide (N2O4)HCID 20195519HCID 20195519, compound

Product 1

HCID 20195502HCID 20195502, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Starting with 3-(4'-bromomethyl phenyl)-2-bromobenzofuran, nitration with dinitrogen tetraoxide in acetic acid in the presence of cyclohexene-4-carboxylic acid provides 3-(4'bromomethyl phenyl)-2-nitrobenzofuran which is reacted according to the method of Example 1 with N,N'-dimethylaminoethylamine. The product obtained is 3-[4'-(N,N'-dimethylaminoethylaminomethyl)phenyl]-2-nitrobenzofuran having the structure ##STR35##

Sources & evidence

ORD record
ord-4e20159507fc42adb28c5805a11c4720
Source dataset
uspto-grants-1985_07
Patent number
US04526896

Reaction notes

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