HCID 23433496, compound → HCID 23433554, compound

HRID 2121806Notes

Reaction equation

HRID 2121806 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][C:9]([CH3:15])([CH3:14])[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]([CH2:8][C:9]([CH3:15])([CH3:14])[CH2:10][NH:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 23433496HCID 23433496, compound

Product 1

HCID 23433554HCID 23433554, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-nitro-1,2,3,4-tetrahydro-3,3-dimethylquinoline (39 mg, 0.187 mmol) in ethyl acetate (2 mL) was hydrogenated under an atmosphere of hydrogen with 10% Pd/C (4 mg) at rt for 2 h. Filtration over Celite™ afforded 30 mg (91%) of 7-amino-1,2,3,4-tetrahydro-3,3-dimethylquinoline (structure 72A of Scheme LII, where R1-2═R5═H, R3-4═methyl) that was used without further purification in the next step. Compound 437 was prepared by General Method 13 (EXAMPLE 147) from 7-amino-1,2,3,4-tetrahydro-3,3-dimethylquinoline (30 mg, 0.17 mmol), ZnCl2 (34 mg, 025 mmol) and ethyl 4,4,4-trifluoroacetoacetate (25 mL, 0.17 mol) to afford 13 mg (26%) of Compound 437 as a yellow solid. Data for Compound 437: 1H NMR (400 MHz, DMSO-d6) 11.71 (bs, 1H), 7.11 (s, 1H), 7.01 (s, 1H), 6.40 (s, 1H), 6.37 (s, 1H), 2.89 (s, 2H), 2.51 (s, 2H), 0.93 (s, 6H).

Workup

  1. filtrationFiltration over Celite™

Sources & evidence

ORD record
ord-d376aef5c65f48e9846d1356295f7e73
Source dataset
uspto-grants-2004_02
Patent number
US06696459B1

Reaction notes

Loading…