Ammonia → 2-Methoxy-N-(4-((4-nitronaphthalen-1-yloxy)methyl)pyridin-2-yl)acetamide

HRID 2069067Notes

Reaction equation

HRID 2069067 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[NH2:7][C:8]1[CH:13]=[C:12]([CH2:14][O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([N+:26]([O-:28])=[O:27])=[CH:18][CH:17]=2)[CH:11]=[CH:10][N:9]=1.CCN(C(C)C)C(C)C.N>C(Cl)Cl.C1COCC1>[CH3:1][O:2][CH2:3][C:4]([NH:7][C:8]1[CH:13]=[C:12]([CH2:14][O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([N+:26]([O-:28])=[O:27])=[CH:18][CH:17]=2)[CH:11]=[CH:10][N:9]=1)=[O:5]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 584167602-Amino-4-((4-nitronaphthalen-1-yloxy)methyl)pyridine

Product 1

HCID 584979032-Methoxy-N-(4-((4-nitronaphthalen-1-yloxy)methyl)pyridin-2-yl)acetamideYield 91.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methoxyacetyl chloride (24.2 mL, 264 mmol) was added dropwise over 10 min to a stirred suspension of the amine (3) (60.0 g, 203 mmol) in a mixture of DCM (300 mL), THF (450 mL) and DIPEA (53.1 mL, 305 mmol) under nitrogen at −5° C. After 10 min the reaction mixture was allowed to warm to RT during which time a dark solution formed. After 30 min a solution of NH3 (7M in MeOH, 30 mL) was added and stirring continued for 1 hr during which time a precipitate formed. The suspension was evaporated in vacuo and the residue was triturated with water (500 mL). The precipitate was collected by filtration, was washed with water (300 mL) and diethyl ether (500 mL) and then dried in vacuo at 60° C. to furnish the title compound (63) as a yellow solid (68 g, 88%): m/z 368 (M+H)+ (ES+).

Workup

  1. customformed
  2. waitcontinued for 1 hr during which time
  3. customa precipitate formed
  4. customThe suspension was evaporated in vacuo
  5. customthe residue was triturated with water (500 mL)
  6. filtrationThe precipitate was collected by filtration
  7. washwas washed with water (300 mL) and diethyl ether (500 mL)
  8. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-f48983d35540416e89bceaf5b38e5bfd
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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