Methylamine → Benzyl 5-[3-(aminooxy)propoxy]-3-chlorobenzoate

HRID 1698861Notes

Reaction equation

O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([Cl:33])[CH:20]=[C:21]([CH:32]=1)[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].CN>O1CCCC1>[NH2:3][O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([Cl:33])[CH:20]=[C:21]([CH:32]=1)[C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of phthalimide 27 (1.00 g, 2.15 mmol) in tetrahydrofuran (20 mL) was added a 40% aqueous solution of methylamine (0.148 mL, 1.72 mmol). After stirring 25 minutes at 0° C., the reaction was evaporated in vacuo, the residue partitioned between methylene chloride and water, and the organic layer dried over Na2SO4 and filtered. The evaporated filtrate was then purified by chromatography on silica gel (40% ethyl acetate in hexanes) giving product 28 (0.576 g, 80%). 1H NMR (300 MHz, CDCl3) δ 7.62 (t, 1H, J=1.6 Hz), 7.48 (dd, 1H, J=2.4 Hz, 1.4 Hz), 7.45-7.32 (m, 5H), 7.08 (t, 1H, J=2.1 Hz), 5.35 (s, 2H), 4.07 (t, 2H, J=6.3 Hz), 3.82 (t, 2H, J=6.3 Hz), 2.07 (pentet, 2H, J=6.3 Hz).

Workup

customthe reaction was evaporated in vacuo
customthe residue partitioned between methylene chloride and water
dry with materialthe organic layer dried over Na2SO4
filtrationfiltered
customThe evaporated filtrate was then purified by chromatography on silica gel (40% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-55aa790831d74389b750dd3982749da4
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06344466B2

Reaction notes

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