Ammonia → Oxane-4-carboxamide

HRID 1664196Notes

Reaction equation

HRID 1664196 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9]C)=O)[CH2:3][CH2:2]1.[NH3:11]>>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH2:11])=[O:9])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

Product 1

HCID 13197203Oxane-4-carboxamideYield 78%

Conditions

Temperature
22 °C

Procedure

A mixture of methyl tetrahydro-2H-pyran-4-carboxylate (7.0 g, 48.6 mmol) and concentrated ammonia (20 ml) was stirred at 22° C. for 18 h. The excess ammonia was then removed under reduced pressure and the residue was crystallized from ethanol to give 4.94 g (78% yield) of the title amide as white crystals: mp 179-181° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.81 (4H, m, 2×CH2), 2.42 (1H, m, CH), 3.44 (2H, m, OCH2), 4.04 (2H, m, OCH2), 5.55 and 5.8 (2×1H, broad, NH2).

Workup

  1. customThe excess ammonia was then removed under reduced pressure
  2. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-ab3f75ef7d9c43a89778d024643dac25
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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