4-(2-(Pyrrolidin-1-yl)ethyl)aniline → 4-{[4-(2-Pyrrolidin-1-yl-ethyl)-phenylamino]-methylene}-1,4-dihydro-2H-isoquinolin-3-one

HRID 2236647Notes

Reaction equation

C[N:2](/[CH:4]=[C:5]1/[C:6](=[O:15])[NH:7][CH2:8][C:9]2[C:14]/1=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:3].[N:16]1([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27]C(N)=[CH:25][CH:24]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1>C1(C)C=CC=CC=1>[N:16]1([CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][C:3]([NH:2][CH:4]=[C:5]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH2:8][NH:7][C:6]3=[O:15])=[CH:27][CH:28]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 0.400 g (1.98 mmol) of (4E)-4-[(dimethylamino)methylene]-1,4-dihydro-3(2H)-isoquinolinone and 0.414 g (2.18 mmol) of 4-(2-Pyrrolidin-1-yl-ethyl)-phenylamine in 4 mL of PhCH3 is heated at 110° C. for 2.5 h. The reaction is placed in a freezer and the precipitated material is collected, washed with cold PhCH3(2×) and Et2O and dried in vacuo to give 0.280 g (41%) of gold crystals: mp 169-173° C. (dec); 1H NMR (DMSO-d6) δ 11.4 (d, 1H, J=11.8 Hz), 8.01 (d, 1H, J=11.8 Hz), 7.63 (m, 2H), 7.16 (s, 4H), 7.07 (m, 2H), 4.40 (s, 2H), 2.60 (m, 4H), 2.50 (m, 2H), 1.67 (s (br), 4H); HRMS (ESI) m/e calcd for C22H25N3O 348.20704. found 348.20588 (M+H)+1.

Workup

customthe precipitated material is collected
washwashed with cold PhCH3(2×) and Et2O
customdried in vacuo

Sources & evidence

ORD record: ord-25e5158445e04c4395ee807ee2f4de4c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713994B2

Reaction notes

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