1,2-Dichloroethane → HCID 3010836, compound

HRID 989662Notes

Reaction equation

HRID 989662 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][N:4]=[C:3]1[C:12]([OH:14])=O.[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:21][C:12]([C:3]2[C:2](=[O:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][N:4]=2)=[O:14])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 660364-ChlorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 3187184-Hydroxycinnoline-3-carboxylic acid

Product 1

HCID 3010836HCID 3010836, compoundYield 7.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Oxo-1,4-dihydro-3-cinnolinecarboxylic acid (0.10 g, 0.53 mmol) is dissolved in 5 mL DMF. To this is added 4-chlorobenzylamine (0.07 ML, 0.58 mmol) and the reaction mixture is stirred at room temperature for 5 min. EDC (0.11 g, 0.57 mmol) and HOBt (0.08 g, 0.56 mmol) are added and the reaction is stirred at room temperature over 2 days. The mixture is poured into 30 mL H2O. A brown precipitate formed which is filtered. The crude product is triturated with hot EtOAc, filtered and dried to yield 0.012 g (7%) of the desired product. Physical characteristics are as follows: m.p. 269-271° C.; 1H NMR (300 MHz, DMSO) δ 14.2, 10.0, 8.17, 7.87, 7.74, 7.56, 7.38, 4.53; MS (fab) m/z 314 (M+H)+, 316, 315, 299, 298, 297, 127, 125, 123, 58.

Workup

  1. stirringthe reaction is stirred at room temperature over 2 days
  2. customA brown precipitate formed which
  3. filtrationis filtered
  4. customThe crude product is triturated with hot EtOAc
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-de1922ba09ac4cf4836e9ef46ca84fe6
Source dataset
uspto-grants-2002_10
Patent number
US06458788B1

Reaction notes

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