Ethyl Acetoacetate → Ethyl 4-amino-5-(heptan-4-yloxy)-2-methylquinoline-3-carboxylate

HRID 1467006Notes

Reaction equation

HRID 1467006 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])[C:3]=1[C:4]#[N:5].O=[C:19]([CH3:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][CH:8]=[CH:7][C:6]=2[O:10][CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])[N:1]=[C:19]([CH3:26])[C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 667456982-Amino-6-(heptan-4-yloxy)benzonitrile

Product 1

HCID 66746658Ethyl 4-amino-5-(heptan-4-yloxy)-2-methylquinoline-3-carboxylate

Procedure

Prepared as in Example 2a from 2-amino-6-(heptan-4-yloxy)benzonitrile (Example 23b) and ethyl 3-oxobutanoate as a pale yellow solid (65%). 1H NMR (400 MHz, DMSO-d6) δ 0.87 (t, J=7.2 Hz, 6H), 1.31 (t, J=7.2 Hz, 3H), 1.47-1.33 (m, 4H), 1.77-1.59 (m, 4H), 2.54 (s, 3H), 4.30 (q, J=7.2 Hz, 2H), 4.67-4.64 (m, 1H), 6.92 (d, J=7.6 Hz, 1H), 7.19 (dd, J=0.8, 8.4 Hz, 1H), 7.49 (t, J=8.0 Hz, 1H), 8.13 (brs, 2H). MS 345 (MH+).

Sources & evidence

ORD record
ord-040b8e9fb5bb4055b77857e5a55897e2
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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