Potassium Carbonate → HCID 178492063, compound

HRID 567704Notes

Reaction equation

HRID 567704 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.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][NH2:27])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]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:27]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 538971714-Chloro-5,6,7,8-tetrahydrocinnoline-3-carboxylic acid ethyl ester

Product 1

HCID 178492063HCID 178492063, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4-Chloro-5,6,7,8-tetrahydrocinnoline-3-carboxylic acid ethyl ester (0.5 g), 4-methoxyphenylhydrazine hydrochloride (0.37 g) and potassium carbonate (0.29 g) in xylene were heated under reflux for 3 h. The solid was collected by filtration, washed with hexane, then water. The residue was absorbed onto silica and purified by flash chromatography using a gradient elution: CH2Cl2 (250 ml), CH2Cl2/(MeOH/NH3 10:1) 99:1 (250 ml), CH2Cl2/(MeOH/NH3 10:1) 98:2 (250 ml), CH2Cl2/(MeOH/NH3 10:1) 97:3 (250 ml), CH2Cl2/(MeOH/NH3 10:1) 96:4 (250 ml), CH2Cl2/(MeOH/NH3 10:1) 95:5 (250 ml). The appropriate fractions were combined and evaporated under reduced pressure to give a solid (79 mg, 13%). δH (360 MHz; DMSO) 1.83 (4H, m, CH2), 2.67 (2H, t, J=5.3 Hz, CH2), 2.72 (2H, d, 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, CH2), m/z (ESP+) 297 (MH+).

Workup

  1. temperatureunder reflux for 3 h
  2. filtrationThe solid was collected by filtration
  3. washwashed with hexane
  4. customThe residue was absorbed onto silica
  5. custompurified by flash chromatography
  6. washa gradient elution
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-af8bad8155464af2a78415761b72c5bb
Source dataset
uspto-grants-2001_01
Patent number
US06180630B2

Reaction notes

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