HCID 59490300, compound → HCID 46830641, compound

HRID 1808030Notes

Reaction equation

[NH2:1][C:2]1[C:11](C#N)=[C:10]2[C:5]([CH2:6][CH:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=3)[C:8]3[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=32)=[CH:4][N:3]=1>Br.C(O)(=O)C>[Cl:25][C:20]1[CH:19]=[C:18]([CH:7]2[CH2:6][C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[CH:11][C:10]=3[C:9]3[CH:14]=[CH:15][CH:16]=[CH:17][C:8]2=3)[CH:23]=[CH:22][C:21]=1[Cl:24]

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 2-amino-6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[f]isoquinoline-1-carbonitrile (186 mg, 0.510 mmol) in 48% hydrobromic acid (1 mL) and 33% wt hydrogen bromide in acetic acid (1 mL) was heated to 200° C. for 45 minutes under microwave irradiation. The mixture was partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (50 mL). The aqueous layer was removed and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by preparative TLC using dichloromethane-methanol (19:1) as eluent to provide 6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[f]isoquinolin-2-amine as an off-white solid (44 mg, 25%). 1H NMR 400 MHz (DMSO-d6) δ 7.80 (d, J=7.6 Hz, 1H), 7.74 (s, 1H), 7.47 (d, J=8 Hz, 1H), 7.41 (t, J=7.2 Hz, 1H), 7.34 (m, 2H), 7.07 (d, J=7.6 Hz, 1H), 6.98 (d, J=8 Hz, 1H), 6.87 (s, 1H), 5.78 (s, 2H), 4.30 (m, 1H), 2.98 (d, J=5.6 Hz, 2H). LCMS m/e 341 (M+H).

Workup

customThe mixture was partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (50 mL)
customThe aqueous layer was removed
dry with materialthe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by preparative TLC

Sources & evidence

ORD record: ord-531a0106086a47be870305b7b8cecd08
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357694B2

Reaction notes

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