Hydrochloric Acid → O-(3-methoxy-4-pent-2-ynyloxy-benzyl)-hydroxylamine

HRID 458247Notes

Reaction equation

HRID 458247 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]#[C:25][CH2:26][CH3:27])[CH2:6][O:7][N:8]1C(=O)C2C(=CC=CC=2)C1=O.O.NN.Cl.O>CO.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]#[C:25][CH2:26][CH3:27])[CH2:6][O:7][NH2:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 184420912-(3-Methoxy-4-pent-2-ynyloxy-benzyloxy)-isoindole-1,3-dione

Product 1

HCID 18442094O-(3-methoxy-4-pent-2-ynyloxy-benzyl)-hydroxylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

2-(3-Methoxy-4-pent-2-ynyloxy-benzyloxy)-isoindole-1,3-dione (27 g, 74 mmol) is suspended in a mixture of 500 ml of methanol and 50 ml of N,N-dimethylformamide. After heating this mixture to +60° C., hydrazine hydrate (8.5 g, 0.17 mol) is added. The reaction is stirred for 3 hours at +60° C. and subsequently cooled down to room temperature. A mixture of 28 ml of concentrated hydrochloric acid and 80 ml of water is added to acidify the resulting suspension. Then it is filtered to remove a precipitation and the solid is washed with water/methanol. The filtrate is concentrated in vacuo to one third of its original volume. Sodium hydroxide (18 g, mol in 90 ml water) is added to the remainder and this mixture is extracted with diethyl ether. The combined organic layer is washed with water and brine, dried over magnesium sulfate and evaporated to give O-(3-methoxy-4-pent-2-ynyloxy-benzyl)-hydroxylamine as yellow oil.

Workup

  1. temperatureAfter heating this mixture to +60° C.
  2. additionis added
  3. filtrationThen it is filtered
  4. customto remove
  5. customa precipitation
  6. washthe solid is washed with water/methanol
  7. concentrationThe filtrate is concentrated in vacuo to one third of its original volume
  8. additionSodium hydroxide (18 g, mol in 90 ml water) is added to the remainder
  9. extractionthis mixture is extracted with diethyl ether
  10. washThe combined organic layer is washed with water and brine
  11. dry with materialdried over magnesium sulfate
  12. customevaporated

Sources & evidence

ORD record
ord-4e89c5c433e7400ab11303db8b8c397b
Source dataset
uspto-grants-2007_03
Patent number
US07189873B2

Reaction notes

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