Cyclopropanecarbonyl chloride → HCID 15675287, compound

HRID 1090145Notes

Reaction equation

HRID 1090145 reaction equation
[C:1]([C:4]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH2:14][CH3:15])=[CH:7][C:5]=1[NH2:6])(=[O:3])[CH3:2].[CH:16]1([C:19](Cl)=[O:20])[CH2:18][CH2:17]1.C1(C2NC3C(C(=O)C=2)=CC(OC)=C(OC)C=3)CC1>C(N(CC)CC)C>[CH:16]1([C:19]([NH:6][C:5]2[CH:7]=[C:8]([O:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[CH:10][C:4]=2[C:1](=[O:3])[CH3:2])=[O:20])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 15675273HCID 15675273, compoundHCID 156752751-(2-Amino-4-ethoxy-5-methoxyphenyl)ethan-1-one

Product 1

HCID 15675287HCID 15675287, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-Acetyl-5-ethoxy-4-metoxyaniline (550 mg), cyclopropylcarbonyl chloride (410 mg) and triethylamine (530 mg) were reacted in the same manner as in the preparation of compound 95 to give N-cyclopropylcarbonyl-2-acetyl-5-ethoxy-4-methoxyaniline (740 mg). The compound (600 mg) and potassium t-butoxide (1.18 g) were reacted in the same manner as in the preparation of compound 95 to obtain 2-cyclopropyl-7-ethoxy-6-methoxy-4(1H)-quinolone (compound 98, 330 mg).

Sources & evidence

ORD record
ord-eb85d842740c4c28b58a8ac911858fef
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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