Ethanol → 3-Amino-2-methoxypyridine

HRID 533951Notes

Reaction equation

HRID 533951 reaction equation
ClC(C[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)C=O.[NH2:12]C(N)=S.[CH2:16]([OH:18])C>>[CH3:16][O:18][C:7]1[C:6]([NH2:12])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 2723790ThioureaHCID 86600156HCID 86600156, compound

Product 1

HCID 27374883-Amino-2-methoxypyridine

Procedure

A mixture of 2-chloro-3-pyridin-3-yl-propionaldehyde (crude from above) and thiourea (14.8 g, 0.194 mol) in ethanol (200 mL) was heated to reflux overnight. The solvent was removed and the residue was diluted with dichoromethane (1.2 L) and then washed with sodium hydroxide (10% aqueous solution, 400 mL) and water (200 mL). The organic layer was extracted three times with hydrochloric acid (5% aqueous solution, 400 mL) and the combined aqueous layer was brought to between pH 9 and 10 with sodium hydroxide (10% aqueous solution). The resulting precipitate was filtered to give the crude product, which was recrystallized, from ethyl acetate and hexanes to give the pure product (5.1 g, 0.023 mol, 5.6% from 2-methoxy-pyridin-3-ylamine). ESI-MS m/z calc. 221.1. found 222.2 (M+1)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed
  4. additionthe residue was diluted with dichoromethane (1.2 L)
  5. washwashed with sodium hydroxide (10% aqueous solution, 400 mL) and water (200 mL)
  6. extractionThe organic layer was extracted three times with hydrochloric acid (5% aqueous solution, 400 mL)
  7. filtrationThe resulting precipitate was filtered
  8. customto give the crude product, which
  9. customwas recrystallized, from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-06715312f8254c74b00442ffa548c093
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Reaction notes

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