1,2-Dichloroethane → HCID 10290951, compound

HRID 1815179Notes

Reaction equation

HRID 1815179 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.CC[N:21]([CH:25]([CH3:27])C)[CH:22]([CH3:24])C.[CH2:28](Cl)[CH2:29]Cl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:4]([C:3]2[C:2]([NH:1][CH2:28][C:29]3[CH:24]=[CH:22][N:21]=[CH:25][CH:27]=3)=[N:10][CH:9]=[CH:8][CH:7]=2)=[O:6])=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 78124-ChloroanilineHCID 729302-Aminonicotinic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 10290951HCID 10290951, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-aminonicotinic acid (5.3 g, 38 mmol) and 4-chloroaniline (4.9 g, 38 mmol) and DIEA (9 ml, 48 mmol) at 0° C. in CH2Cl2 was added EDC (9.5 g, 48 mmol) and HOBt (5.1 g, 38 mmol), the reaction was warmed to RT and stirred overnight. The solvent was evaporated under reduced pressure and quenched with 2N NaOH solution (60 ml) and stirred for 20 min. The precipitate was filtered to give the titled compound. MS (ES+): 248 (M+H)+; (ES−): 246 (M−H)−.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customquenched with 2N NaOH solution (60 ml)
  3. stirringstirred for 20 min
  4. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-17635c66fc404dfb98bb6d4c4e717b92
Source dataset
uspto-grants-2005_04
Patent number
US06878714B2

Reaction notes

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