Sodium Carbonate → N-(4-((4-aminonaphthalen-1-yloxy)methyl)pyridin-2-yl)-2-methoxy acetamide

HRID 2069068Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([N+:25]([O-])=O)=[CH:17][CH:16]=2)[CH:10]=[CH:9][N:8]=1)=[O:5].C(=O)([O-])[O-].[Na+].[Na+]>CC(O)=O.[Fe]>[NH2:25][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([O:14][CH2:13][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:16][CH:17]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of the nitroarene (63) (30.0 g, 82.0 mmol) and iron powder (22.8 g, 408 mmol) in AcOH (300 mL) was heated at 50° C. for 1.5 hr, and was then cooled to RT. Solid sodium carbonate was added portionwise to the reaction mixture until effervescence was no longer observed. The mixture was extracted with ethyl acetate (2×700 mL) and the combined organic extracts were washed with saturated aqueous sodium carbonate and with brine and then dried (MgSO4). Evaporation in vacuo furnished the title compound (Intermediate M) as a brown solid (25.0 g, 77%): m/z 338 (M+H)+ (ES+).

Workup

temperaturewas then cooled to RT
extractionThe mixture was extracted with ethyl acetate (2×700 mL)
washthe combined organic extracts were washed with saturated aqueous sodium carbonate and with brine
dry with materialdried (MgSO4)
customEvaporation in vacuo

Sources & evidence

ORD record: ord-07553471f0b4456184334ccfff84133a
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299073B2

Reaction notes

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