Phenylhydrazine → HCID 178515216, compound

HRID 252942Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17]CC)=O.[C:20]1([NH:26][NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(N(CC)CC)C>[N+:12]([C:9]1[CH:8]=[CH:7][C:6]2[NH:5][CH:4]=[C:3]3[C:15](=[O:17])[N:26]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:27]=[C:2]3[C:11]=2[CH:10]=1)([O-:14])=[O:13]

Participants

Conditions

Temperature: 135 °C

Procedure

In a vial were added 4a, phenyl hydrazine and triethylamine. The vial was sealed and heated to 135° C. for 12 hours. The product was collected by filtration and was washed with methanol in 85% yield. 1H-NMR (DMSO-d6) δ (ppm): 7.19 (1H, tt, J=7.32, 1.22 Hz), 7.42 (2H, t, J=7.56 Hz), 7.84 (1H, d, J=9.03 Hz), 8.16 (2H, dd, J=8.30, 1.22 Hz), 8.82 (1H, s), 8.89 (1H, d, J=2.44 Hz). m/z 307.3 (MH+).

Workup

customThe vial was sealed
filtrationThe product was collected by filtration
washwas washed with methanol in 85% yield

Sources & evidence

ORD record: ord-128324d750de41988354997e8c115a5c
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872002B2

Reaction notes

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