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

HRID 2069112Notes

Reaction equation

HRID 2069112 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.[CH3:31][O:32][CH2:33][C:34](Cl)=[O:35].N>C(Cl)Cl.CO>[CH3:31][O:32][CH2:33][C:34]([NH:21][C:17]1[CH:16]=[C:15]([O:14][C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:20]=[CH:19][N:18]=1)=[O:35]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 585325624-(4-Nitronaphthalen-1-yloxy)pyridin-2-amine

Product 1

HCID 674524762-Methoxy-N-(4-(4-nitronaphthalen-1-yloxy)pyridin-2-yl)acetamideYield 98.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 4-(4-nitronaphthalen-1-yloxy)pyridin-2-amine (71.8 g, 255 mmol) in dry DCM (1.1 L) and DIPEA (84.0 mL, 511 mmol), cooled in an ice bath, was added dropwise 2-methoxyacetyl chloride (35.0 mL, 383 mmol) over 20 min. The resulting red solution was stirred at RT for 1 hr and was then treated with a solution of NH3 in MeOH (7 M, 100 mL). A precipitate formed immediately and the reaction mixture was stirred for a further 15 min and the volatiles were evaporated in vacuo. The solid residue was triturated with water (900 mL), collected by filtration and washed with water (2×250 mL) to give the title compound as a yellow solid (89.1 g, 96%): m/z 354 (M+H)+ (ES+).

Workup

  1. temperaturecooled in an ice bath
  2. customA precipitate formed immediately
  3. stirringthe reaction mixture was stirred for a further 15 min
  4. customthe volatiles were evaporated in vacuo
  5. customThe solid residue was triturated with water (900 mL)
  6. filtrationcollected by filtration
  7. washwashed with water (2×250 mL)

Sources & evidence

ORD record
ord-ab1d138e81ea4d5f952085ed25ec6dd4
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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