Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1) → HCID 178515273, compound

HRID 567706Notes

Reaction equation

HRID 567706 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][CH:22]=[CH:21][C:20]=1[NH:25][NH2:26]>C1(C)C(C)=CC=CC=1>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[C:4](=[O:5])[C:6]2=[N:7][NH:8][C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[C:15]2=[N:26]1

Participants

4

Reactant 2

HCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)HCID 538971714-Chloro-5,6,7,8-tetrahydrocinnoline-3-carboxylic acid ethyl ester

Product 1

HCID 178515273HCID 178515273, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4-Chloro-5,6,7,8-tetrahydrocinnoline-3-carboxylic acid ethyl ester (0.5 g), 2-fluorophenylhydrazine hydrochloride (0.34 g) and H{umlaut over (u)}nig's base (0.73 ml) in xylene were heated under reflux for 3 h. The solvent was evaporated under reduced pressure and the residue purified by flash chromatography using a gradient elution: CH2Cl2 (500 ml), CH2Cl2/(MeOH/NH3 10:1) 99:1 (500 ml), CH2Cl2/(MeOH/NH3 10:1) 98:2 (500 ml), CH2Cl2/(MeOH/NH3 10:1) 97:3 (500 ml), CH2Cl2/(MeOH/NH3 10:1) 96:4 (500 ml), CH2Cl2(MeOH/NH3 10:1) 95:5 (500 ml). The appropriate fractions were combined and evaporated under reduced pressure to give a solid (250 mg, 42%). δH (360 MHz; DMSO) 1.83 (4H, m, CH2), 2.61 (2H, t, J=5.3 Hz, CH2), 2.75 (2H, t, J=5.3 Hz, CH2), 7.30-7.57 (4H, m, ArH), m/z (ESP+) 285 (MH+). C15H13FN4O requires C, 63.37; H, 4.61; N, 19.71; found C, 63.18; H, 4.70; N, 19.35%.

Workup

  1. temperatureunder reflux for 3 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue purified by flash chromatography
  4. washa gradient elution
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-45ac74d52877472ab726c14bc0f2c5e9
Source dataset
uspto-grants-2001_01
Patent number
US06180630B2

Reaction notes

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