Ethyl 4-chloroacetoacetate → HCID 66746480, compound

HRID 1467147Notes

Reaction equation

HRID 1467147 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][CH2:12]2)[C:3]=1[C:4]#[N:5].ClCC(=O)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[NH2:5][C:4]1[C:3]2[C:6]([O:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)=[CH:7][CH:8]=[CH:9][C:2]=2[N:1]=[C:25]2[CH2:24][O:23][C:21](=[O:22])[C:20]=12

Participants

3

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 66745877HCID 66745877, compound

Product 1

HCID 66746480HCID 66746480, compound

Procedure

Prepared as in Example 2a from 2-amino-6-(cyclohexyloxy)benzonitrile (Example 36b) and ethyl 4-chloro-3-oxobutanoate as an orange solid (29%). 1H NMR (400 MHz, DMSO-d6) δ 1.30-1.72 (m, 8H), 2.04-2.08 (m, 2H), 4.70 (m, 1H), 5.26 (s, 2H), 7.09 (d, J=8.0 Hz, 1H), 7.36 (d, J=8.0 Hz, 1H), 7.64 (m, 2H), 8.14 (brs, 1H). MS 299 (MH+).

Sources & evidence

ORD record
ord-1992288a9e9c453196fc723acc565c93
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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