1,2-Dichloroethane → 4-[4-(Methylamino)-3-nitrophenoxy]pyridine-2-carboxamide

HRID 2070346ノート

反応式

HRID 2070346 の反応式
[CH3:1][NH:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14](O)=[O:15])[CH:9]=2)=[CH:5][C:4]=1[N+:19]([O-:21])=[O:20].C(Cl)CCl.C1C=[N:30]C2N(O)N=NC=2C=1.[Cl-].[NH4+]>O1CCCC1>[CH3:1][NH:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([NH2:30])=[O:15])[CH:9]=2)=[CH:5][C:4]=1[N+:19]([O-:21])=[O:20]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 181649HOAtHCID 220404974-[4-(Methylamino)-3-nitrophenoxy]pyridine-2-carboxylic acid

生成物 1

HCID 597899824-[4-(Methylamino)-3-nitrophenoxy]pyridine-2-carboxamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 4-[4-(methylamino)-3-nitrophenoxy]pyridine carboxylic acid in tetrahydro-furan was added EDC (2 eq) and HOAT (1.5 eq) and ammonium chloride (2 eq). The resulting mixture was stirred at ambient temperature for 16 h. The mixture was concentrated and partitioned between ethylacetate and water. A solid crashes out in the aqueous layer which was filtered and was found to be the product on LC/MS. The organic layer was then dried with sodium sulfate and concentrated. Purification on silica gel gave 4-[4-(methylamino)-3-nitrophenoxy]pyridine-2-carboxamide.

後処理

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethylacetate and water
  3. filtrationA solid crashes out in the aqueous layer which was filtered
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. concentrationconcentrated
  6. customPurification on silica gel

出典と根拠

ORDレコード
ord-5d1ca246938449c18df57381e25f6e82
出典データセット
uspto-grants-2012_10
特許番号
US08299108B2

反応ノート

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