Ethyl Acetoacetate → Ethyl 4-amino-5-((2-methoxycyclohexyl)oxy)-2-methylquinoline-3-carboxylate

HRID 2047848Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]2[O:17][CH3:18])[C:3]=1[C:4]#[N:5].O=[C:20]([CH3:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>>[CH2:25]([O:24][C:22]([C:21]1[C:20]([CH3:27])=[N:1][C:2]2[C:3]([C:4]=1[NH2:5])=[C:6]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][CH3:18])[CH:7]=[CH:8][CH:9]=2)=[O:23])[CH3:26]

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 667466302-Amino-6-(2-methoxycyclohexyloxy)benzonitrile

Product 1

HCID 66746044Ethyl 4-amino-5-((2-methoxycyclohexyl)oxy)-2-methylquinoline-3-carboxylate

Procedure

Prepared as in Example 2a from 2-Amino-6-(2-methoxycyclohexyloxy)benzonitrile (Example 109b) and ethyl 3-oxobutanoate as a pale yellow oil (16%). MS 359 (MH+).

Sources & evidence

ORD record: ord-e96a836b8a5e463eb5a6c7e904ffd882
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592592B2

Reaction notes

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