Diethyl acetonedicarboxylate → HCID 10924650, compound

HRID 2047738Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].O=[C:11]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>>[CH2:22]([O:21][C:19]([C:18]1[C:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:1][C:2]2[C:3]([C:4]=1[NH2:5])=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:20])[CH3:23]

Participants

Reactant 2

HCID 66045Diethyl acetonedicarboxylate

HCID 729132-Aminobenzonitrile

Product 1

HCID 10924650HCID 10924650, compound

Procedure

Prepared as in Example 2a from 2-aminobenzonitrile and diethyl 3-oxopentanedioate as a pale yellow solid (25%). 1H NMR (400 MHz, DMSO-d6) δ 1.19 (t, J=8.0 Hz, 3H), 1.30 (t, J=8.0 Hz, 3H), 4.08 (m, 4H), 4.28 (q, J=8.0 Hz, 2H), 7.50 (m, 1H), 7.73 (m, 2H), 8.10 (bs, 2H), 8.53 (d, J=8.0 Hz, 1H). MS 303 (MH+).

Sources & evidence

ORD record: ord-601e78c7607d42188ef1d509fb64af31
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592592B2

Reaction notes

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