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

HRID 2070346Notes

Reaction equation

HRID 2070346 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5d1ca246938449c18df57381e25f6e82
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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