Aniline → HCID 86649925, compound

HRID 1803220Notes

Reaction equation

CC1(C)O[C:6](=[O:8])[CH:5]([C:9](=[O:24])[CH2:10][CH2:11][CH2:12][C:13]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:17][CH2:16][CH2:15][O:14]2)C(=O)O1.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C(C)=CC=CC=1>[O:24]=[C:9]([CH2:10][CH2:11][CH2:12][C:13]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:14][CH2:15][CH2:16][O:17]1)[CH2:5][C:6]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:8]

Participants

Conditions

Temperature: 140 °C

Procedure

Step AAH (4): To a solution of 2,2-dimethyl-5-(4-(2-phenyl-1,3-dioxolan-2-yl)butanoyl)-1,3-dioxane-4,6-dione (4.0 g, 11.04 mmol) in xylene (30 mL) was added aniline (1.21 mL, 13.3 mmol). The r×n was stirred at 140° C. for 2 h. The crude reaction contents were directly loaded onto silica gel and purified by silica gel column chromatography (60% EtOAc/hexanes) to afford 3-oxo-N-phenyl-6-(2-phenyl-1,3-dioxolan-2-yl)hexanamide (3.0 g, 77% yield). 1H NMR (500 MHz, chloroform-d) δ ppm 9.16 (br. s., 1 H) 7.54 (d, J=7.63 Hz, 2 H) 7.44 (d, J=7.02 Hz, 2 H) 7.28-7.39 (m, 5 H) 7.12 (t, J=7.48 Hz, 1 H) 3.97-4.07 (m, 2 H) 3.72-3.82 (m, 2 H) 3.53 (s, 2 H) 2.60 (t, J=7.32 Hz, 2 H) 1.89-1.97 (m, 2 H) 1.67-1.79 (m, 2 H).

Workup

customThe crude reaction contents
custompurified by silica gel column chromatography (60% EtOAc/hexanes)

Sources & evidence

ORD record: ord-434bfb251b344be5b0f335f232750be7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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