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

HRID 2069068
Notes
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Reaction equation

HRID 2069068 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 584979032-Methoxy-N-(4-((4-nitronaphthalen-1-yloxy)methyl)pyridin-2-yl)acetamide

Product 1

HCID 45256716N-(4-((4-aminonaphthalen-1-yloxy)methyl)pyridin-2-yl)-2-methoxy acetamideYield 90.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic Acid
Solvent

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

  1. temperaturewas then cooled to RT
  2. extractionThe mixture was extracted with ethyl acetate (2×700 mL)
  3. washthe combined organic extracts were washed with saturated aqueous sodium carbonate and with brine
  4. dry with materialdried (MgSO4)
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes