HCID 23433475, compound → HCID 23433648, compound

HRID 1604813Notes

Reaction equation

HRID 1604813 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]([CH3:14])[CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]([CH3:14])[CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 23433475HCID 23433475, compound

Product 1

HCID 23433648HCID 23433648, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-nitro-1,2,3,4-tetrahydro-4-methylquinoline (36 mg, 0.172 mmol) in ethyl acetate (3 mL) was hydrogenated under an atmosphere of hydrogen with 10% Pd/C (4 mg) at rt for 2 h. Filtration over Celite™ afforded 26 mg (85%) of 7-amino-1,2,3,4-tetrahydro-4-methylquinoline (structure 61A of Scheme XLVIII, where R1-3 =H, R4 =methyl) that was used without further purification for the next step. The title compound was prepared by General Method 13 (EXAMPLE 147) form 7-amino-1,2,3,4-tetrahydro-4-methylquinoline (26 mg, 0.145 mmol), ZnCl2 (30 mg, 0.218 mmol) and ethyl 4,4,4-trifluoroacetoacetate (21 mL, 0.145 mol) to afford 0.8 mg (2%) of 1,2,3,4-tetrahydro-4-methyl-6-trifluoromethyl-8-pyridono[5,6-g]quinoline (Compound 425). Data for Compound 425: 1H NMR (400MHz, DMSO-d6) 11.65 (bs, 1H), 7.20 (s, 1H), 6.96 (s, 1H), 6.37 (s, 2H), 3.25 (m, 2H), 2.90 (m, 1H), 1.84 (m, 1H), 1.59 (m, 1H), 1.20 (d, J=6.9, 3H).

Workup

  1. filtrationFiltration over Celite™

Sources & evidence

ORD record
ord-f4f593b9eb2a4f1f850239ca2117793e
Source dataset
uspto-grants-1999_11
Patent number
US05994544

Reaction notes

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