Potassium Hydroxide → Ammonia

HRID 500632Notes

Reaction equation

HRID 500632 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]([CH3:41])([CH3:40])[CH2:23][CH2:24][C:25]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:26]#[N:27])[CH2:18][CH2:17]3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH-:42].[K+]>CC(C(O)C)CC>[NH3:19].[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:15][CH:16]3[CH2:17][CH2:18][N:19]([C:22]([CH3:41])([CH3:40])[CH2:23][CH2:24][C:25]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:26]([NH2:27])=[O:42])[CH2:20][CH2:21]3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59423956HCID 59423956, compound

Product 2

HCID 222AmmoniaHCID 59423977HCID 59423977, compound

Reagents, catalysts & solvents 1

HCID 112613-Methylpentan-2-olSolvent

Procedure

A suspension of the product of example 97 (70 mg, 0.13 mmol) and powdered potassium hydroxide (144 mg, 2.57 mmol) in 3-methyl-4-pentanol (4 mL) was heated under reflux for 36 hours. The reaction mixture was allowed to cool to room temperature and the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate (30 mL) and water (20 mL). The organic layer was separated, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 95:5:0.5 to 90:10:1. Appropriate fractions were concentrated in vacuo and the residue further purified by chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 98:2:0.2 to 95:5:0.5, to afford the title compound as a gum in 21% yield.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 36 hours
  3. customthe solvent removed under reduced pressure
  4. customThe residue was partitioned between ethyl acetate (30 mL) and water (20 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with dichloromethane
  10. concentrationAppropriate fractions were concentrated in vacuo
  11. customthe residue further purified by chromatography on silica gel
  12. washeluting with dichloromethane

Sources & evidence

ORD record
ord-78debe3094f94ca3940a1fb74af55e76
Source dataset
uspto-grants-2010_08
Patent number
US07772223B2

Reaction notes

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