Ammonia → Ethyl 4-amino-6-ethoxyquinoline-3-carboxylate

HRID 1466992Notes

Reaction equation

HRID 1466992 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[NH3:20]>>[NH2:20][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 727468ethyl 4-chloro-6-ethoxyquinoline-3-carboxylate

Product 1

HCID 49758106Ethyl 4-amino-6-ethoxyquinoline-3-carboxylate

Procedure

Prepared as in Example 1a from ethyl 4-chloro-6-ethoxyquinoline-3-carboxylate (Example 13b) and ammonia as an off white solid (77%). 1H NMR (400 MHz, DMSO-d6) δ 1.31-1.40 (m, 6H), 4.15 (q, J=7.2 Hz, 2H), 4.31 (q, J=6.8 Hz, 2H), 7.34 (q, J=6.4 Hz, 1H), 7.69-7.74 (m, 2H), 8.21 (bs, 2H), 8.77 (s, 1H). MS 261 (MH+).

Sources & evidence

ORD record
ord-cfd3efc88d0a4580899a89bf6edaacd7
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

Loading…