Ammonia → HCID 70268047, compound

HRID 1638235Notes

Reaction equation

HRID 1638235 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[CH:5]O[C:3]=1[CH2:10][OH:11].[NH3:12]>>[CH3:1][CH:2]1[C:7](=[O:8])[C:6]([CH3:9])=[CH:5][N:12]=[C:3]1[CH2:10][OH:11]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 11062593HCID 11062593, compound

Product 1

HCID 70268047HCID 70268047, compoundYield 96%

Conditions

Temperature
60 °C

Procedure

3,5-Dimethyl-2-hydroxymethyl-4-pyrone 4 (9.75 g, 63.3 mmol) was dissolved in 32% aqueous ammonia (0.880, 60 ml) in a 100 ml round bottom flask. The flask was sealed with a septum cap and made secure with wire. The solution was then stirred at 60° C. for 48 hours before being evaporated to dryness under reduced pressure to give 5 as an off-white solid (9.30 g, 60.8 mmol, 96% yield). Selected IR (cm-1, nujol) 3150-3500 (br, s), 1639 (s); 1H-NMR (DMSO-d6) δ 1.80 (s, 3H), 1.84 (s, 3H), 4.45 (s, 2H), 7.44 (s, 1H); Ms (APCI+) m/z (%) 154 (MH+, 100).

Workup

  1. customThe flask was sealed with a septum
  2. customcap
  3. custombefore being evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e4c622e566234ab5852cbb1f4889627a
Source dataset
uspto-grants-2000_03
Patent number
US06043371

Reaction notes

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