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Ammonium Chloride → 2-(2,2,2-Trifluoroethoxy)pyridin-3-amine

HRID 46466
Notes
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Reaction equation

HRID 46466 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+]([O-])=O)=[CH:7][N:6]=1.[Cl-].[NH4+:17]>[Fe].C(O)C>[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[C:10]([NH2:17])=[CH:9][CH:8]=[CH:7][N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 6137185-Nitro-2-(2,2,2-trifluoroethoxy)pyridine

Product 1

HCID 167853012-(2,2,2-Trifluoroethoxy)pyridin-3-amineYield 23.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

2-(2,2,2-Trifluoroethoxy)-5-nitropyridine (5.0 grams), powdered iron (15 grams), and ammonium chloride (25 grams) were refluxed in 3A ethanol until TLC detected no starting material (about 4 hours). The reaction mixture was filtered, washed with water, and solvents removed, yielding 1.0 gram of the product as a thin brownish liquid. NMR confirmed the identity of the product.

Workup

  1. customno starting material (about 4 hours)
  2. filtrationThe reaction mixture was filtered
  3. washwashed with water, and solvents
  4. customremoved

Sources & evidence

ORD record
ord-3817a0ce2dd540c5b34efa23b714c16d
Source dataset
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04173639

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes