Benzylamine → HCID 57949507, compound

HRID 2427637Notes

Reaction equation

CO[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:5]=1[CH2:12]Br.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[CH2:15]([N:22]1[CH2:12][C:5]2[C:4](=[CH:9][CH:8]=[CH:7][C:6]=2[O:10][CH3:11])[C:3]1=[O:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromomethyl-3-methoxy-benzoic acid methyl ester (0.119 g, 0.5 mmol), benzylamine (0.065 mL, 0.6 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-benzyl-4-methoxy-2,3-dihydro-isoindol-1-one (0.078 g, 61.4%). 1H NMR (300 MHz, CDCl3): δ (ppm) 3.83 (s, 3H), 4.21 (s, 2H), 4.69 (s, 2H), 6.98 (d, 1H), 7.25-7.51 (m, 7H). GC-MS: m/z 253 (M)+, 176 (M-77)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-b58551bade1748ea8e47053f53c2f71f
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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