HCID 22279055, compound → HCID 23433536, compound

HRID 850350Notes

Reaction equation

HRID 850350 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](=[O:15])[NH:9][O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[CH3:16].C(ON[C:23]([C:25]1[CH:34]=C2[C:28](C(C)=CC(C)(C)N2)=[CH:27][CH:26]=1)=O)(C)(C)C>>[C:11]([O:10][NH:9][C:8]([C:4]1[C:3]([CH3:16])=[C:2]2[C:7]([C:27]([CH3:28])=[CH:26][C:25]([CH3:34])([CH3:23])[NH:1]2)=[CH:6][CH:5]=1)=[O:15])([CH3:12])([CH3:13])[CH3:14]

Participants

3

Reactant 2

HCID 22279055HCID 22279055, compoundHCID 23433661HCID 23433661, compound

Product 1

HCID 23433536HCID 23433536, compoundYield 84%

Procedure

This compound was prepared from 2-amino-6-tert-butyloxycarbamoyltoluene (4.00 g, 18.0 mmol) in a manner similar to that described for 7-tert-butyloxycarbamoyl-1,2-dihydro-2,2,4-trimethylquinoline (EXAMPLE 13), affording 4.56 g (84%) of the desired dihydroquinoline as a white solid. Data for 7-tert-butyloxycarbamoyl-1,2-dihydro-2,2,4,8-tetramethylquinoline: 1H NMR (400 MHz, CDCl3) 6.94 and 6.88 (br ABq, 2H, JAB ·8.3 Hz, 6,5-H), 6.16 (br s, 1H, HNBoc), 5.27 (s, 1H, 3-H), 3.61 [br s, 1H, (CH3)2CNH], 2.04 (s, 3H, 8-CH3), 1.97 (s, 3H, 4-CH3), 1.50 [s, 9H, (CH3)3CO)], 1.28 [s, 6H, 2-(CH3)2 ].

Sources & evidence

ORD record
ord-46c3ca7962ca4a0dbb7f9ac7bc033919
Source dataset
uspto-grants-2000_01
Patent number
US06017924

Reaction notes

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