4-Fluorophenylhydrazine hydrochloride → HCID 178515275, compound

HRID 567705Notes

Reaction equation

HRID 567705 reaction equation
C(O[C:4]([C:6]1[N:7]=[N:8][C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[C:15]=1Cl)=[O:5])C.Cl.[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][NH2:26])=[CH:21][CH:20]=1>C1(C)C(C)=CC=CC=1>[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:4](=[O:5])[C:6]3=[N:7][NH:8][C:9]4[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=4[C:15]3=[N:26]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 538971714-Chloro-5,6,7,8-tetrahydrocinnoline-3-carboxylic acid ethyl ester

Product 1

HCID 178515275HCID 178515275, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4-Chloro-5,6,7,8-tetrahydrocinnoline-3-carboxylic acid ethyl ester (0.5 g), 4-fluorophenylhydrazine hydrochloride (0.34 g) and H{umlaut over (u)}inig's base (0.73 ml) in xylene under nitrogen were heated under reflux for 2 h. The solid was collected by filtration, washed with diethyl ether, water and diethyl ether. The residue was recrystallised from ethanol to give the title compound (136 mg, 13%). δH (360 MHz; DMSO-d6) 1.83 (4H, m, CH2), 2.67 (2H, t, J=5.3 Hz, CH2), 2.72 (2H, t, J=5.3 Hz, CH2), 3.78 (3H, s, OCH3), 7.02 (2H, d, J=9 Hz, ArH), 8.06 (2H, d, J=9 Hz, ArH), m/z (ESP+) 285 (MH+). C15H13FN4O requires C, 63.37; H, 4.61; N, 19.71; found C, 62.96; H, 4.36; N, 19.48%.

Workup

  1. temperatureunder reflux for 2 h
  2. filtrationThe solid was collected by filtration
  3. washwashed with diethyl ether, water and diethyl ether
  4. customThe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-6e2b0e3f90604678aca1570edbff232d
Source dataset
uspto-grants-2001_01
Patent number
US06180630B2

Reaction notes

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