4-Iodoaniline → N-Cyclopropylaniline

HRID 1067937Notes

Reaction equation

HRID 1067937 reaction equation
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(O[C:12]1(O[Si](C)(C)C)[CH2:14][CH2:13]1)C.C([BH3-])#N.[Na+]>>[CH:12]1([NH:6][C:5]2[CH:7]=[CH:8][CH:2]=[CH:3][CH:4]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 108934-IodoanilineHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 7016287N-Cyclopropylaniline

Procedure

4-Iodoaniline (F-0) is reductively alkylated with [(1-ethoxycyclopropyl)oxy]trimethylsilane and sodium cyanoborohydride to give the N-cyclopropyl aniline (F-1). Treatment with diethyl ethoxymethylenemalonate in pyridine affords the enamine (F-2) which is cyclized with polyphosphoric acid to the quinoline (F-3). Treatment with p-chlorobenzylamine at elevated temperature converts the ester to the amide (F-4). Palladium catalyzed coupling of the iodide with propargyl alcohol affords F-5. Reaction with platinum and hydrogen gas affords the saturated propyl alcohol (F-6).

Sources & evidence

ORD record
ord-f9acdf1dec514b68bad4efa5032a1875
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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