Hydrazine hydrate (1:1) → HCID 89375802, compound

HRID 1752257Notes

Reaction equation

HRID 1752257 reaction equation
[CH:1]([C:3]1[O:8][CH2:7][CH2:6][CH2:5][C:4]=1[C:9]([O:11]CC)=O)=O.O.[NH2:15][NH2:16]>CO>[O:8]1[C:3]2[CH:1]=[N:15][NH:16][C:9](=[O:11])[C:4]=2[CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 89375787HCID 89375787, compound

Product 1

HCID 89375802HCID 89375802, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred 0° C. mixture of ethyl 6-formyl-3,4-dihydro-2H-pyran-5-carboxylate (1.705 g, 9.26 mmol) in methanol (80 mL) was added very quickly 35% hydrazine hydrate (0.311 g, 9.72 mmol). After 20 minutes, the solvent was removed under reduced pressure, and the residue was treated with acetic acid (70 mL) and water (7 mL) and stirred at 110° C. for 20 minutes. The solvents were removed in vacuo. The crude residue was eluted by silica gel chromatography with a 0 to 25% gradient of methanol/dichloromethane to afford the title compound (1.384 g) as a light yellow solid in better than 90% purity. MS (ESI) [m/e, (M+H)+]=153.2. 1H NMR (400 MHz, chloroform-d) δ ppm 10.56 (br s, 1H), 7.53 (s, 1H), 4.17-4.35 (m, 2H), 2.57 (t, J=6.57 Hz, 2H), 1.99-2.08 (m, 2H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionthe residue was treated with acetic acid (70 mL) and water (7 mL)
  3. customThe solvents were removed in vacuo
  4. washThe crude residue was eluted by silica gel chromatography with a 0 to 25% gradient of methanol/dichloromethane

Sources & evidence

ORD record
ord-f7d82551f17048febafc97110da45c48
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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