1,2-Dichloroethane → HCID 12267035, compound

HRID 238483Notes

Reaction equation

HRID 238483 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.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:4]([NH:16][C:15]2[CH:17]=[CH:18][C:12]([Cl:11])=[CH:13][CH:14]=2)=[O:6])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

7

Reactant 5

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

Product 1

HCID 12267035HCID 12267035, 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-f606ac7288be48eb9ea32946ea61f697
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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