2-Methoxyaniline → HCID 24985363, compound

HRID 388101Notes

Reaction equation

HRID 388101 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])[C:5]([N+:17]([O-])=O)=[CH:4][CH:3]=1.ClC1C([N+]([O-])=O)=CC=C(Cl)N=1.C[O:32][C:33]1[C:34](N)=[CH:35][CH:36]=[CH:37][CH:38]=1.C(NC(C)C)(C)C.[O:47]1CCC[CH2:48]1>>[OH:32][C:33]1[CH:34]=[C:35]([C:2]2[N:7]=[C:6]3[N:8]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[O:15][CH3:16])[C:48](=[O:47])[NH:17][C:5]3=[CH:4][CH:3]=2)[CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 5

HCID 70002-MethoxyanilineHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 852392,6-Dichloro-3-nitropyridineHCID 2842435HCID 2842435, compound

Product 1

HCID 24985363HCID 24985363, compoundYield 81%

Conditions

Temperature
-78 °C

Procedure

6-Chloro-N-(2-methoxyphenyl)-3-nitropyridin-2-amine. 2,6-Dichloro-3-nitropyridine (3.0 g, 15.54 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to −78° C. A solution of o-anisidine (1.91 g, 15.54 mmol) and diisopropylamine (2.10 g, 16.31 mmol) in tetrahydrofuran (5 mL) was added dropwise. The mixture was stirred at ambient temperature for 16 h. The solution was condensed under reduced pressure and partitioned between water and ethyl acetate (3×), organics were pooled and dried over magnesium sulfate, filtered and solvent removed under reduced pressure to give the crude product. The solid was triturated with ethyl acetate/hexanes and the resultant precipitate filtered to afford the title compound (3.53 g, 81%). MS (ESI) m/z 280.1 [M+1]+.

Workup

  1. customcondensed under reduced pressure
  2. custompartitioned between water and ethyl acetate (3×)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customsolvent removed under reduced pressure
  6. customto give the crude product
  7. customThe solid was triturated with ethyl acetate/hexanes
  8. filtrationthe resultant precipitate filtered

Sources & evidence

ORD record
ord-6e10736223f54c0caa212308179fc9b3
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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