Methyl chloroformate → N-Hydroxy-N-methyl-3-(3-phenoxyphenyl)prop-2-enamide

HRID 649238Notes

Reaction equation

HRID 649238 reaction equation
ClC(OC)=O.[O:6]([C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[CH:16]=[CH:17][C:18](O)=[O:19])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.Cl.[CH3:32][NH:33][OH:34]>O1CCCC1.O.C(OCC)(=O)C>[O:6]([C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[CH:16]=[CH:17][C:18]([N:33]([CH3:32])[OH:34])=[O:19])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 77906N-methylhydroxylamine hydrochlorideHCID 735855HCID 735855, compound

Product 1

HCID 53836491N-Hydroxy-N-methyl-3-(3-phenoxyphenyl)prop-2-enamideYield 48%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl chloroformate (2.6 ml) was added dropwise to a solution of m-phenoxycinnamic acid (8 g) and triethylamine (18.5 g) in tetrahydrofuran (60 ml) at 0°. A solution of N-methylhydroxylamine hydrochloride (5.6 g) in water (5 ml) was added, and the mixture was stirred for 2 hours. Isolation with ethyl acetate afforded 3-phenoxy-N-methylcinnamohydroxamic acid (ca 4.3 g), m.pt. 124°-125° [from ethyl acetate/light petroleum (b.pt. 60°-80° C.)]. The m-Phenoxycinnamic acid used as starting material was prepared by condensation of m-phenoxybenzaldehyde with malonic acid in the presence of piperidine and pyridine.

Sources & evidence

ORD record
ord-951615666bce4d32ada8634bfb0b79dd
Source dataset
uspto-grants-1988_04
Patent number
US04738986

Reaction notes

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