Hydrazine → HCID 178434212, compound

HRID 253229Notes

Reaction equation

HRID 253229 reaction equation
O[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:19](=O)[CH3:20].[NH2:22][NH2:23]>C(O)COCCO>[CH3:20][C:19]1[C:3]2[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[C:10]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[CH:11][C:2]=2[NH:23][N:22]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 668908751-[2-Hydroxy-4-(4-hydroxyphenyl)napthalen-1-yl]ethanone

Product 1

HCID 178434212HCID 178434212, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A solution of 1-[2-hydroxy-4-(4-hydroxyphenyl)napthalen-1-yl]ethanone (0.223 g, 0.8 mmol), and 35% aqueous hydrazine (0.72 mL, 8.0 mmol) in diethylene glycol (2.7 mL) was heated using a reflux condenser in a 170° C. oil bath for 12 h, then 190° C. for 2 h until 95% complete conversion was observed. The crude solution was purified directly via preparative reverse phase HPLC (CH3CN/H2O/TFA eluent) to give 0.132 g (60% yield) of 4-(1-methyl-3H-benzo[e]indazol-5-yl)phenol. 1H NMR (400 MHz, d6-DMSO): 9.62 (broad s, 1H), 8.37 (d, 1H), 7.82 (d, 1H), 7.65 (dt, 1H), 7.42 (dt, 1H), 7.39 (s, 1H), 7.30 (dd, 2H), 6.93 (s, 2H), 2.82 (s, 3H); MS (EI) for C18H14N2O: 275 (MH+).

Workup

  1. customin a 170° C.
  2. customfor 12 h
  3. customThe crude solution was purified directly via preparative reverse phase HPLC (CH3CN/H2O/TFA eluent)

Sources & evidence

ORD record
ord-4d9245bed31243b4a7947bd6998aab67
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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