HCID 23433465, compound → 7-Tert-butyloxycarbamoyl-1,2,3,4-tetrahydro-2,2,8-trimethylquinoline

HRID 2294415Notes

Reaction equation

HRID 2294415 reaction equation
[C:1]([O:5][NH:6][C:7]([C:9]1[C:18]([CH3:19])=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH3:21])([CH3:20])[NH:16]2)=[CH:11][CH:10]=1)=[O:8])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][NH:6][C:7]([C:9]1[C:18]([CH3:19])=[C:17]2[C:12]([CH2:13][CH2:14][C:15]([CH3:21])([CH3:20])[NH:16]2)=[CH:11][CH:10]=1)=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 23433465HCID 23433465, compound

Product 1

HCID 234336297-Tert-butyloxycarbamoyl-1,2,3,4-tetrahydro-2,2,8-trimethylquinolineYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-tert-butyloxycarbamoyl-1,2-dihydro-2,2,8-trimethylquinoline (114 mg, 0.39 mmol) in 4 mL of ethyl acetate was hydrogenated under an atmosphere of hydrogen with Pd-C 10% (11 mg) at rt for 7 h. Filtration over Celite afforded 60 mg (60%) of 7-tert-butyloxycarbamoyl-1,2,3,4-tetrahydro-2,2,8-trimethylquinoline. The title compound was prepared by General Method 12 (EXAMPLE 147) from 7-tert-butyloxycarbamoyl-1,2,3,4-tetrahydro-2,2,8-trimethylquinoline (60 mg, 0.206 mmol) to afford 30 mg (77%) of 7-amino-1,2,3,4-tetrahydro-2,2,8-trimethylquinoline as a light reddish oil. Data for 7-amino-1,2,3,4-tetrahydro-2,2,8-trimethylquinoline: 1 H NMR (400 MHz, CDCl3) 6.70 (d, J=7.9, 1H), 6.09 (d, J=7.9, 1H), 3.30 (bs, 3H), 2.71 (t, J=6.7, 2H), 1.89 (s, 3H), 1.65 (t, J=6.7, 2H), 1.21 (s, 6H).

Workup

  1. filtrationFiltration over Celite

Sources & evidence

ORD record
ord-5f6079679593465bb6d1ab090ab01b71
Source dataset
uspto-grants-1997_11
Patent number
US05688808

Reaction notes

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