Sodium hydride → HCID 54413294, compound

HRID 225137Notes

Reaction equation

HRID 225137 reaction equation
[C:1]([O:9][CH:10]1[CH2:19][CH2:18][C:17]2[NH:16][C:15](=[O:20])[CH2:14][CH2:13][C:12]=2[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21](OC1CC=C2C(CCC(=O)N2)C1)(=O)[C:22]1C=CC=C[CH:23]=1.C(I)CC.[H-].[Na+]>>[CH2:21]([N:16]1[C:17]2[CH2:18][CH2:19][CH:10]([O:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11][C:12]=2[CH2:13][CH2:14][C:15]1=[O:20])[CH2:22][CH3:23]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 12902700HCID 12902700, compoundHCID 12902701HCID 12902701, compound

Product 1

HCID 54413294HCID 54413294, compound

Procedure

Following the above procedure, 59 g. of a mixture of 6-benzoyloxy-3,4,5,6,7,8-hexahydro-2(1H)-quinolinone and 6-benzoyloxy-3,4,4a,5,6,7-hexahydro-2(1H)-quinolinone were reacted with n-propyl iodide in the presence of sodium hydride to yield 1-n-propyl-6-benzoyloxy-3,4,5,6,7,8-hexahydro-2-(1H)-quinolinone and the corresponding 3,4,4a,5,6,7-hexahydro isomer. The compounds were purified by chromatography over florisil using an ether-chloroform solvent mixture as the eluant. Also following the above procedure, a mixture of the 1-benzyl-6-benzoyloxyhexahydro-2(1H)-quinolinones was prepared by substituting benzyl bromide for methyl iodide.

Sources & evidence

ORD record
ord-915035caf9e3458986951e6489178af3
Source dataset
uspto-grants-1980_11
Patent number
US04235909

Reaction notes

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