2-Nitrobenzaldehyde → HCID 5170752, compound

HRID 426880Notes

Reaction equation

[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[CH:12]1([C:15]([CH3:17])=[O:16])[CH2:14][CH2:13]1>>[CH:12]1([C:15]([CH:17]=[CH:6][C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])=[O:16])[CH2:14][CH2:13]1

Participants

Reactant 2

HCID 111012-Nitrobenzaldehyde

HCID 13004Cyclopropyl methyl ketone

Product 1

HCID 5170752HCID 5170752, compound

Procedure

2-Nitrobenzaldehyde is condensed with methyl cyclopropyl ketone to give 2-(2-nitrophenyl)vinyl cyclopropyl ketone. The latter is reduced selectively with hydroxylamine and hydroxylamine O-sulfonic acid in dilute sodium hydroxide solution to yield 2-(2-nitrophenyl)ethyl cyclopropyl ketone, which is then reduced with sodium borohydride to 2-(2-nitrophenyl)ethyl cyclopropyl carbinol. The carbinol is treated in the usual way with phosphorus tribromide and zinc bromide to afford 4-[6-(2-nitrophenyl)-3-hexenyl] bromide. The latter is reacted with potassium iodide, potassium carbonate and 3,5-heptanedione to produce 4-[6-(2-nitrophenyl)-3-hexenyl]-3,5-heptanedione which is selectively reduced with hydroxylamine and hydroxylamine O-sulfonic acid to give the title compound.

Sources & evidence

ORD record: ord-80da58a6c1044de4a1c1bf1206efc95e
Source dataset: uspto-grants-1979_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04171378

Reaction notes

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