Aniline → HCID 178500877, compound

HRID 227105Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([CH3:14])[CH:8]=1)=[O:6].[C:16](OC)(OC)(OC)[CH3:17].C(OC(=O)C)(=O)C.[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[CH3:1][O:2][C:3](=[O:15])[C:4]([C:5](=[O:6])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([CH3:14])[CH:8]=1)=[C:16]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:17]

Participants

Reactant 4

HCID 6115Aniline

HCID 7918Acetic Anhydride

HCID 15050Trimethyl orthoacetate

HCID 2758622Methyl 3-(3,4-dimethylphenyl)-3-oxopropanoate

Product 1

HCID 178500877HCID 178500877, compound

Procedure

10.6 g (51.4 mmol) of 3-(3,4-dimethyl-phenyl)-3-oxo-propionic acid methyl ester was heated with 12.4 g (103 mmol) of trimethyl orthoacetate and 5.51 g (54.0 mmol) of acetic anhydride at 115° C. for 3 days. The mixture was evaporated and combined with 4.69 mL (51.4 mmol) of aniline. Yield: 8.60 g of a yellow solid (after flash chromatography contains inseparable 3-(3,4-dimethyl-phenyl)-3-oxo-propionic acid methyl ester): LC-MSD, m/z for C20H21NO3 [M+H]+=324.2; HPLC retention time: 2.1 min.

Workup

customThe mixture was evaporated

Sources & evidence

ORD record: ord-a46123a9b22842f7a4fb68b909dbc946
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557213B2

Reaction notes

Loading…