2,2,4-trimethyl-1,2-dihydroquinolin-7-amine → HCID 10631958, compound

HRID 850351Notes

Reaction equation

HRID 850351 reaction equation
C(ONC([C:9]1[C:18]([CH3:19])=[C:17]2[C:12]([C:13]([CH3:22])=[CH:14][C:15]([CH3:21])([CH3:20])[NH:16]2)=[CH:11][CH:10]=1)=O)(C)(C)C.[NH2:23]C1C=C2C(C(C)=CC(C)(C)N2)=CC=1>>[NH2:23][C:9]1[C:18]([CH3:19])=[C:17]2[C:12]([C:13]([CH3:22])=[CH:14][C:15]([CH3:21])([CH3:20])[NH:16]2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 2817922,2,4-trimethyl-1,2-dihydroquinolin-7-amineHCID 23433536HCID 23433536, compound

Product 1

HCID 10631958HCID 10631958, compound

Procedure

Removal of the Boc protective group of 7-tert-butyloxycarbamoyl-1,2-dihydro-2,2,4,8-tetramethylquinoline (400 mg, 1.32 mmol) was effected in the manner similar to that described for 7-amino-1,2-dihydro-2,2,4-trimethylquinoline (EXAMPLE 13), affording 267 mg (quantitative) of the desired aniline as a light reddish oil. Data for 7-amino-1,2-dihydro-2,2,4,8-tetramethylquinoline: 1H NMR (400 MHz, CDCl3) 6.82 (d, 1H, J=8.2 Hz, 5-H), 6.08 (d, 1H, J=8.1 Hz, 6-H), 5.15 (d, 1H, J=1.2 Hz, 3-H), 3.56 (br s, 3H, NH2, NH), 1.95 (d, 3H, J=1.2 Hz, 4-CH3), 1.91 (s, 3H, 8-CH3), 1.27 [s, 6H, 2-(CH3)2 ].

Sources & evidence

ORD record
ord-ed69b89ad04f4f3299ca7eedc459ef9b
Source dataset
uspto-grants-2000_01
Patent number
US06017924

Reaction notes

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