Ethyl Acetoacetate → HCID 66746396, compound

HRID 1466974Notes

Reaction equation

HRID 1466974 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[C:4]#[N:5].[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=O>>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][CH:8]=[C:7]([O:10][CH3:11])[CH:6]=2)[N:1]=[C:14]([CH3:16])[C:13]=1[C:12]([O:18][CH2:19][CH3:20])=[O:17]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 35130022-Amino-5-methoxybenzonitrile

Product 1

HCID 66746396HCID 66746396, compound

Procedure

Prepared as in Example 2a from 2-amino-5-methoxybenzonitrile (Campbell, J. B. et al. Synth. Commun. 1989, 19, 2255-2263.) and ethyl acetoacetate as an off-white solid (92%). 1H NMR (400 MHz, DMSO-d6) δ 1.33 (t, J=6.8 Hz, 3H), 2.57 (s, 3H), 3.86 (s, 3H), 4.33 (q, J=6.8 Hz, 2H), 7.28 (dd, J=2.8, 9.2 Hz, 1H), 7.59 (d, J=9.2 Hz, 1H), 7.60 (bs, 2H), 7.63 (d, J=2.8 Hz, 1H). MS 261 (MH+).

Sources & evidence

ORD record
ord-5a27a326921d469e964f94d55a595c40
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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