1,2,3,4-Tetrahydro-1-methylquinoline → 1,2,3,4-Tetrahydroquinoline

HRID 893061

Reaction equation

HRID 893061 reaction equation
Cl.C[N:3]1[C:12]2[C:7](=[CH:8][C:9](N=O)=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.CN1C2C(=CC=CC=2)CCC1>>[NH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1

Participants

3

Reactant 2

HCID 681091,2,3,4-Tetrahydro-1-methylquinolineHCID 190990131-Methyl-6-nitroso-1,2,3.4-tetrahydroquinoline hydrochloride

Product 1

HCID 694601,2,3,4-Tetrahydroquinoline

Procedure

1-methyl-6-nitroso-1,2,3.4-tetrahydroquinoline hydrochloride ##STR25## The title compound is prepared from 1-methyl1,2,3,4-tetrahydroquinoline (obtained from 1,2,3,4tetrahydroquinoline by heating with trimethylphosphate (according to Huisgen et al., Chem. Ber. 92, 203 (1959)). The crude product is produced in the usual manner analogous to Examples 10 and 11 and purified on silica gel 60 (Merck) with isopropanol/n-butylacetate/water=5:3:2. The title compound is obtained by dissolving this in acetone after addition of ethereal hydrochloric acid, m.p. 123°-124° C. (decomp.), TLC: silica gel 60, mobile phase: isopropanol/n-butylacetate/water=5:3:2, Rf =0.7.

Sources & evidence

ORD record
ord-dae7ceedec2d48afba15df48ed72fbf0
Source dataset
uspto-grants-1992_06
Patent number
US05122244

Linked notes

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