Potassium Carbonate → 4-(4-Amino-2-chlorophenoxy)picolinamide

HRID 2237265ノート

反応式

HRID 2237265 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.CC([O-])(C)C.[K+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([C:23]([NH2:25])=[O:24])[CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([C:23]([NH2:25])=[O:24])[CH:18]=2)=[C:4]([Cl:9])[CH:3]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 775784-Amino-2-chlorophenolHCID 3035434-Chloropyridine-2-carboxamideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 435176714-(4-Amino-2-chlorophenoxy)picolinamide収率 40.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-amino-2-chlorophenol (Aldrich, 430 mg, 3.0 mmol) in DMF (2.0 mL) at room temperature was added KOt-Bu (352 mg, 3.2 mmol). The mixture was allowed to stir at room temperature for 1 h. To the solution were then added 4-chloropicolinamide (468 mg, 3.0 mmol) and K2CO3 (221 mg, 1.6 mmol). The resulting suspension was heated at 90° C. overnight. After cooling down, the suspension was diluted with 100 mL of EtOAc and 50 mL of H2O. The organic layer was separated and washed with brine (2×25 mL) and dried over MgSO4. After filtration and concentration, the solid was triturated with 50 mL of DCM. The solid was then collected and washed with DCM (2×20 mL), EtOAc (5.0 mL) and dried to give 4-(4-amino-2-chlorophenoxy)picolinamide (320 mg, 40% yield). MS(ESI+): m/z 264.12/266.07 (M+H)+.

後処理

  1. temperatureThe resulting suspension was heated at 90° C. overnight
  2. temperatureAfter cooling down
  3. customThe organic layer was separated
  4. washwashed with brine (2×25 mL)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration and concentration
  7. customthe solid was triturated with 50 mL of DCM
  8. customThe solid was then collected
  9. washwashed with DCM (2×20 mL), EtOAc (5.0 mL)
  10. customdried

出典と根拠

ORDレコード
ord-3d7ad592781843fab5845b99602ba322
出典データセット
uspto-grants-2010_05
特許番号
US07714138B2

反応ノート

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