4-Chloroanisole → HCID 54188056, compound

HRID 1112202Notes

Reaction equation

HRID 1112202 reaction equation
[CH2:1]([O:3]C(=O)CC(CC1C=CC=CC=1)=O)C.[CH2:16]([O:18][C:19](=[O:30])[CH2:20][CH:21]([NH2:29])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:17].[C:31]1([O:38][CH3:39])[CH:36]=[CH:35][C:34](Cl)=[CH:33][CH:32]=1>>[CH2:16]([O:18][C:19](=[O:30])[CH2:20][CH:21]([NH:29][C:1](=[O:3])[C:34]1[CH:35]=[CH:36][C:31]([O:38][CH3:39])=[CH:32][CH:33]=1)[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:17]

Participants

4

Reactant 3

HCID 121674-ChloroanisoleHCID 225855Ethyl 3-oxo-4-phenylbutanoateHCID 11161478149193-77-1

Product 1

HCID 54188056HCID 54188056, compound

Procedure

γ-Phenylacetoacetic acid ethyl ester was converted into 3-amino-4-phenylbutyric acid ethyl ester (M.P. of hydrogen oxalate 151°-153°). Further reaction with p-anisolyl chloride gave 3-p-methoxybenzamido-4-phenylbutyric acid ethyl ester (M.P. 102°-104°). A Bischler-Napieralski reaction (boiling with phosphorus oxychloride) gave 3,4-dihydro-1-p-methoxyphenyl-3-isoquinolinylacetic acid ethyl ester. Hydrogenation using a palladium/charcoal (10% w /w) gave cis-1-p-methoxyphenyl-1,2,3,4-tetrahydro-3-isoquinolinylacetic acid ethyl ester.

Sources & evidence

ORD record
ord-7af62e21011b4da1a99fd76b65a709d4
Source dataset
uspto-grants-1978_10
Patent number
US04120965

Reaction notes

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