Ethyl Acetoacetate → HCID 66746631, compound

HRID 2047864Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[C:4]#[N:5].O=[C:18]([CH3:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>>[CH2:23]([O:22][C:20]([C:19]1[C:18]([CH3:25])=[N:1][C:2]2[C:3]([C:4]=1[NH2:5])=[C:6]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:7]=[CH:8][CH:9]=2)=[O:21])[CH3:24]

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 22136223HCID 22136223, compound

Product 1

HCID 66746631HCID 66746631, compound

Procedure

Prepared as in Example 2a from 2-amino-6-phenoxybenzonitrile and ethyl 3-oxobutanoate as a yellow oil (72%). 1H NMR (400 MHz, DMSO-d6) δ 1.32 (t, J=8.0 Hz, 3H), 2.59 (s, 3H), 4.33 (q, J=8.0 Hz, 2H), 6.61 (dd, J=8.0 Hz, 1H), 7.16 (d, J=4.0 Hz, 2H), 7.25 (t, J=8.0 Hz, 1H), 7.39-7.52 (m, 4H), 7.93 (brs, 2H). MS 323 (MH+).

Sources & evidence

ORD record: ord-48fc915d8f814515af8c62a580f86fc0
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592592B2

Reaction notes

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