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

HRID 2070346노트

반응식

HRID 2070346 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5d1ca246938449c18df57381e25f6e82
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299108B2

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