Aniline → 3-Methyl-N-phenylbut-2-enamide

HRID 1440425Notes

Reaction equation

HRID 1440425 reaction equation
C([N:4]1[C:13]2[C:8](=[CH:9][C:10](N)=[CH:11][CH:12]=2)[C:7]([CH3:16])([CH3:15])[CH2:6][C:5]1=[O:17])(C)C.CC(C)=CC(Cl)=O.NC1C=CC=CC=1>>[CH3:15][C:7]([CH3:16])=[CH:6][C:5]([NH:4][C:13]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:17]

Participants

4

Reactant 3

HCID 6115Aniline2×HCID 1023943-Methyl-2-butenoyl chloride2×HCID 15479546HCID 15479546, compound2×

Product 1

HCID 123870223-Methyl-N-phenylbut-2-enamide

Procedure

Reaction Scheme 4 illustrates the synthesis of N-isopropyl 4,4-dimethyl-2-oxo-6-aminoquinoline (Compound 34), which is used in accordance with Reaction Scheme 1 to synthesize exemplary Compound 8 of the present invention. Thus, 3,3-dimethylacryloyl chloride (Compound 35, available from Aldrich) is reacted with aniline (Compound 36) to yield N-3,3-dimethylacryloyl aniline (Compound 37). Compound 37 is ring closed under Friedel Crafts conditions to yield 4,4-dimethyl-2-oxoquinoline (Compound 38) which is thereafter alkylated with iso-propyl iodide to give N-isopropyl 4,4-dimethyl-2-oxoquinoline (Compound 39). Nitration of Compound 39 yields N-isopropyl 4,4-dimethyl-2-oxo-6-nitroquinoline Compound 40, which is reduced with hydrogen on palladium to give Compound 34.

Workup

  1. customReaction Scheme 4
  2. customis used in accordance with Reaction Scheme 1

Sources & evidence

ORD record
ord-78e887422cdf4ebcaa8139401fa247dd
Source dataset
uspto-grants-1996_03
Patent number
US05498755

Reaction notes

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