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

HRID 2047731Notes

Reaction equation

HRID 2047731 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]>>[CH2:18]([O:17][C:15]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH2:20])=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[CH:8][CH:7]=2)=[O:16])[CH3:19]

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-bd17f80dba9149698f6122f6742b8fd5
Source dataset
uspto-grants-2013_11
Patent number
US08592592B2

Reaction notes

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