1,2-Dichloroethane → HCID 135525315, compound

HRID 1455503Notes

Reaction equation

HRID 1455503 reaction equation
C(Cl)CCl.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[C:22]([C:23](O)=[O:24])=[CH:21][C:20]2[C:15](=[CH:16][C:17]([O:26]C)=[CH:18][CH:19]=2)[N:14]=1.[CH:28]1[CH:29]=[CH:30][C:31]2N(O)N=[N:34][C:32]=2[CH:33]=1.NC1C=CC=CC=1>CN(C=O)C.C(Cl)Cl>[C:32]1([NH:34][C:23]([C:22]2[C:13]([NH:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[Cl:5])=[N:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[C:17]([OH:26])[CH:16]=3)=[O:24])[CH:33]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 9858643HCID 9858643, compound

Product 1

HCID 135525315HCID 135525315, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

EDC (633 mg, 3.3 mmol) was added to a solution of 2-(2-Chloro-phenylamino)-7-methoxy-quinoline-3-carboxylic acid (986 mg, 3.0 mmol), HOBt (446 mg, 3.3 mmol) and aniline (307 mg, 3.3 mmol) in DMF (5 ml) at room temperature. After stirring the mixture for 1 hr, CH2Cl2 was used to extract the reaction mixture, and washed with water, saturated brine and then dried with magnesium sulfate. The solvent was removed under reduced pressure to give yellow oil. The yellow oil was purified by chromatography on SCX column using MeOH as eluent. At last, 2-(2-Chloro-phenylamino)-7-hydroxy-quinoline-3-carboxylic acid phenylamide was obtained as yellow solid after recrystallization from CH2Cl2 and Hexane; 947 mg (78%).

Workup

  1. extractionto extract the reaction mixture
  2. washwashed with water, saturated brine
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customto give yellow oil
  6. customThe yellow oil was purified by chromatography on SCX column

Sources & evidence

ORD record
ord-00b0080823d042edb078e8ad7c6199fc
Source dataset
uspto-grants-2009_01
Patent number
US07482455B2

Reaction notes

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