Diphenylmethylidenehydrazine → N-benzhydrylidene-N'-isoquinolin-5-yl-hydrazine

HRID 222106Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[C:12](=[N:25][NH2:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:12](=[N:25][NH:26][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 5-bromoisoquinoline (32 mmol), benzophenone hydrazone (32 mmol), BINAP (0.32 mmol) and palladium acetate (0.32 mmol) in dry and degassed toluene (15 mL), sodium tert-butoxide (44.9 mmol) was added together with 16 mL of dry, degassed toluene. The mixture was heated at 80° C. for 4 h, cooled to rt and filtered through a celite pad, rinsing with diethyl ether. The crude product was purified by semi -automatic liquid chromatography on silica gel (eluant: hexane/AcOEt 7:3) affording the title compound (65% yield). ESI (+) MS: m/z 324 (MH+). 1H NMR: 7.36 (d, J=6.10, 1H), 7.38-7.45 (m, 2H), 7.48-7.53 (m, 2H), 7.58 (m, 8H), 7.88 (d, J=6.34, 1H), 8.39 (d, J=5.97, 1H), 8.76 (s, 1H), 9.24 (s, 1H).

Workup

customin dry
additionwas added together with 16 mL
customof dry
customdegassed toluene
temperaturecooled to rt
filtrationfiltered through a celite pad
washrinsing with diethyl ether
customThe crude product was purified by semi -automatic liquid chromatography on silica gel (eluant: hexane/AcOEt 7:3)

Sources & evidence

ORD record: ord-aa5ba939ed794e9f9e9f05c8f9168801
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207180B2

Reaction notes

Loading…