Sodium Carbonate → N-(4-(4-Aminonaphthalen-1-yloxy)pyridin-2-yl)-2-methoxyacetamide

HRID 239031Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N+:24]([O-])=O)=[CH:16][CH:15]=2)[CH:10]=[CH:9][N:8]=1)=[O:5].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.[Fe]>[NH2:24][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([O:13][C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][O:2][CH3:1])[CH:12]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A stirred suspension of 2-methoxy-N-(4-(4-nitronaphthalen-1-yloxy)pyridin-2-yl)acetamide (11) (44.0 g, 125 mmol) and iron powder (41.7 g, 747 mmol) in acetic acid (300 mL) was heated at 45° C. After 3 hr the mixture was cooled to RT and poured slowly and cautiously onto solid Na2CO3 (200 g). The mixture effervesced vigorously. The mixture was partitioned between water (500 mL) and EtOAc (500 mL). The aqueous layer was basified with solid Na2CO3 to pH 11 and filtered through a pad of celite. The aqueous layer and celite pad were extracted with EtOAc (3×500 mL) and the combined extracts were washed with saturated aqueous NaHCO3 solution (500 mL), dried (MgSO4) and evaporated in vacuo to afford N-(4-(4-aminonaphthalen-1-yloxy)pyridin-2-yl)-2-methoxyacetamide (12) (35.0 g, 78%) as a purple foam: m/z 324 (M+H)+ (ES+).

Workup

temperatureAfter 3 hr the mixture was cooled to RT
customThe mixture was partitioned between water (500 mL) and EtOAc (500 mL)
filtrationfiltered through a pad of celite
extractionThe aqueous layer and celite pad were extracted with EtOAc (3×500 mL)
washthe combined extracts were washed with saturated aqueous NaHCO3 solution (500 mL)
dry with materialdried (MgSO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-3b1dbdd4c37c4c72ba8902f369a9acf2
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642773B2

Reaction notes

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