Ethanol → 2-(Hydrazinecarbonyl)benzoic acid
Reaction equation
ClC1C(C(C2C=C3C(C=CC(C4C=CC=CC=4)=N3)=CC=2)N2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])=NC=CN=1.[NH2:36][NH2:37].C(Cl)Cl.CC[OH:43]>>[C:17]([NH:36][NH2:37])(=[O:18])[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:10]([OH:19])=[O:43]Participants
Procedure
A solution of 2-[(3-chloropyrazin-2-yl)-(2-phenylquinolin-7-yl)-methyl]-isoindole-1,3-dione (1.536 g, 3.22 mmol) and anhydrous hydrazine (335 μL, 342 mg, 10.7 mmol) in EtOH (2 mL)/CH2Cl2 (12 mL) is stirred at rt overnight. The white precipitate formed (phthalic hydrazide) is filtered off and washed with CH2Cl2. The combined filtrate and washings are concentrated in vacuo, the residue is suspended in CDCl3 and filtered (0.45 μM pore size), and the filtrate is concentrated in vacuo to obtain the title compound as yellow foam, which is used for the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 2.4 (brs, 2H), 5.79 (s, 1H), 7.43-7.55 (m, 3H), 7.61 (dd, J=1.8, 8.6 Hz, 1H), 7.81 (d, J=8.4Hz, 1H), 7.86 (d, J=8.4 Hz, 1H), 8.06 (d, J=1.2 Hz, 1H), 8.10-8.15 (m, 2H), 8.19 (d, J=8.8 Hz, 1H), 8.31 (d, J=2.4 Hz, 1H), 8.60 (d, J=2.4 Hz, 1H). MS (ES+): m/z 347.0/349.0 (30/10) [MH+], 330.0/332.0 (18/6) [MH+−NH3]. HPLC: tR=2.1 min (MicromassZQ, polar—5 min).
Sources & evidence
- ORD record
- ord-7eafcb918c1b468494409cc85da69683
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101613B2
Reaction notes
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