Water → 1-(5-Nitropyridin-2-yl)azetidin-3-ol

HRID 1948779Notes

Reaction equation

HRID 1948779 reaction equation
Cl.[OH:2][CH:3]1[CH2:6][NH:5][CH2:4]1.Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=1.C(N(CC)CC)C.O>CN(C)C=O.C(OCC)(=O)C>[OH:2][CH:3]1[CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=2)[CH2:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 783082-Chloro-5-nitropyridineHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 529372641-(5-Nitropyridin-2-yl)azetidin-3-olYield 92.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.311 g (2.84 mmol) of 3-hydroxyazetidine hydrochloride, 0.3 g (1.89 mmol) of 2-chloro-5-nitropyridine and 0.41 ml (2.84 mmol) of triethylamine in 10 ml of dimethylformamide is heated overnight at 100° C. After this period of time, the suspension is poured into a mixture of 30 ml of water and 30 ml of ethyl acetate. The aqueous phase is separated and then extracted with 20 ml of ethyl acetate. The organic phases are combined, washed three times with 25 ml of water and then dried over sodium sulphate and concentrated under reduced pressure. 0.34 g of the expected product is thus obtained in the form of a solid which will be used as it is in the subsequent synthesis.

Workup

  1. waitAfter this period of time
  2. customThe aqueous phase is separated
  3. extractionextracted with 20 ml of ethyl acetate
  4. washwashed three times with 25 ml of water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-369bce6bbdd245fdb6dc16a77f842dc7
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

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