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

HRID 239030Notes

Reaction equation

HRID 239030 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.C(O)(=O)C>[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 92.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(4-nitronaphthalen-1-yloxy)pyridin-2-amine (10) (40.0 g, 135 mmol) and DIPEA (48.1 mL, 270 mmol) in DCM (600 mL) at 0° C., under nitrogen, was added dropwise methoxyacetyl chloride (18.53 ml, 203 mmol). The mixture was warmed to RT and after 1 hr a solution of ammonia (100 mL, 7 M in MeOH) was added and stirring continued for 30 min, during which time a precipitate formed. The mixture was evaporated in vacuo and water (1 L) was added to the residue to provide a red suspension. Glacial acetic acid was added dropwise until a yellow colour persisted (˜5 mL). The solid was collected by filtration and washed with water (300 mL) to afford 2-methoxy-N-(4-(4-nitronaphthalen-1-yloxy)pyridin-2-yl)acetamide (11) (44.1 g, 90%) as a yellow solid: m/z 354 (M+H)+ (ES+).

Workup

  1. additionwas added
  2. customa precipitate formed
  3. customThe mixture was evaporated in vacuo and water (1 L)
  4. additionwas added to the residue
  5. customto provide a red suspension
  6. filtrationThe solid was collected by filtration
  7. washwashed with water (300 mL)

Sources & evidence

ORD record
ord-ec6dbab17abd4f2ba1103405d39ed86d
Source dataset
uspto-grants-2014_02
Patent number
US08642773B2

Reaction notes

Loading…