Ethanol → 2-(Hydrazinecarbonyl)benzoic acid
Reaction equation
ClC1C(C(C2C=C3C(C=CC=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.[NH2:30][NH2:31].C(Cl)Cl.CC[OH:37]>>[C:17]([NH:30][NH2:31])(=[O:18])[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:10]([OH:19])=[O:37]Participants
Procedure
A solution of 2-[(3-chloropyrazin-2-yl)-quinolin-7-ylmethyl]-isoindole-1,3-dione (789 mg, 1.97 mmol) and anhydrous hydrazine (63 μL, 64 mg, 2.0 mmol) in EtOH (4 mL)/CH2Cl2 (2 mL) was stirred at ambient temperature for 1 d. More hydrazine (93 μL, 95 mg, 3.0 mmol) was added, and stirring was continued for 2 d. The solid formed (phthalic hydrazide) was filtered off and washed with EtOH, and the combined filtrate and washings were dried to yield a red, sticky solid. This solid was suspended in CH2Cl2 and filtered, and the filtrate was concentrated to give the title compound as an orange gum; 1H NMR (CDCl3, 400 MHz) δ 2.4 (brs, 2H), 5.79 (s, 1H), 7.39 (dd, J=4.2, 8.2 Hz, 1H), 7.64 (dd, J=1.8, 8.6 Hz, 1H), 7.81 (d, J=8.4 Hz, 1H), 8.01 (d, J=0.8 Hz, 1H), 8.13 (dd, J=0.8, 8.0 Hz, 1H), 8.31 (d, J=2.4 Hz, 1H), 8.59 (d, J=2.4 Hz, 1H), 8.90 (dd, J=1.6, 4.4 Hz, 1H); MS (ES+): m/z 271.0/273.0 (30/10) [MH+], 254.1/256.1 (30/10) [MH+−NH3].
Sources & evidence
- ORD record
- ord-18b3e6da26424eda9e5a0e01eb0c8214
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101613B2
Reaction notes
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