Hydrazine hydrate (1:1) → HCID 68294613, compound

HRID 2279503Notes

Reaction equation

HRID 2279503 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([N:13]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:10][O:11][CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8].O.NN>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH2:13])[CH2:10][O:11][CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86705497HCID 86705497, compound

Product 1

HCID 68294613HCID 68294613, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 196 (2.0 g, 5.7 mmol) and THF:MeOH (1:1, 20 mL) at RT was added hydrazine monohydrate (2.9 g, 57 mmol) and the reaction was heated to 50° C. for 18 h. The reaction was cooled to RT, filtered, and the filtrate was poured into water and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered, and concentrated. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:30) to afford 1.1 g (88%) of (S)-1-(3,4-dichlorophenyl)-2-methoxyethanamine as a off-white solid (198).

Workup

  1. temperatureThe reaction was cooled to RT
  2. filtrationfiltered
  3. additionthe filtrate was poured into water
  4. extractionextracted with DCM
  5. dry with materialThe combined organic fractions were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by SiO2 chromatography
  9. washeluting with DCM/MeOH (500:30)

Sources & evidence

ORD record
ord-5ec76fb795eb4833871069f1bd98b731
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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