Hydrazine → HCID 42602276, compound

HRID 1867641Notes

Reaction equation

[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][O:7][CH2:8][C:9]1([CH2:18][CH2:19][N:20]2C(=O)C3C(=CC=CC=3)C2=O)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][O:10]1.NN>C(O)C.CCOCC>[F:36][C:34]([F:35])([F:37])[C:32]1[CH:31]=[C:5]([CH:4]=[C:3]([C:2]([F:39])([F:38])[F:1])[CH:33]=1)[CH2:6][O:7][CH2:8][C:9]1([CH2:18][CH2:19][NH2:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][O:10]1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 2-(2-(1-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-1,3-dihydroisobenzofuran-1-yl)ethyl)isoindoline-1,3-dione (250 mg, 0.455 mmol) in ethanol (2 mL) was added hydrazine (0.100 mL, 3.2 mmol). The resulting solution was heated to 45° C. and held there for 3 h. The reaction was cooled to room temperature, diluted with ether, and filtered to remove the precipitate which was discarded. Concentration of the mother liquor gave 175 mg (92%) as a colorless oil. 1H-NMR (CDCl3, 300 MHz) δ 7.74 (s, 1H), 7.63 (s, 2H), 7.28 (m, 2H), 7.21 (m, 1H), 7.16 (m, 1H), 5.11 (s, 2H), 4.61 (qAB, JAB=12.8 Hz, 2H), 3.65 (qAB, JAB=9.8 Hz, 2H), 2.73 (m, 1H), 2.54 (m, 1H), 2.13 (ddd, J=14.4, 8.6, 5.8 Hz, 1H), 2.00 (ddd, J=14.3, 8.6, 5.8 Hz, 1H), 1.55 (bs, 2H); 13C-NMR (CDCl3, 126 MHz) δ 141.4, 141.3, 139.9, 131.7 (q, J=33.6 Hz), 128.2, 127.5, 127.1, 123.4 (q, J=273 Hz), 121.7, 121.4, 121.1, 90.0, 76.8, 72.8, 72.0, 40.4, 37.4. Mass spec.: 420.14 (MH)+. Accurate mass spec.: m/z 420.1391 [MH]+, Δ=1.7 ppm.

Workup

temperatureThe reaction was cooled to room temperature
filtrationfiltered
customto remove the precipitate which
customConcentration of the mother liquor gave 175 mg (92%) as a colorless oil

Sources & evidence

ORD record: ord-9b4fbe95243c4e5ab6d0abc935f1d8e1
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632861B2

Reaction notes

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