Hydrochloric Acid → HCID 19439680, compound

HRID 1734021Notes

Reaction equation

HRID 1734021 reaction equation
O.NN.C1(=O)[N:8]([CH2:9][C:10]2[CH:11]=[C:12]([C:18](=[O:20])[CH3:19])[CH:13]=[CH:14][C:15]=2[O:16][CH3:17])C(=O)C2=CC=CC=C12.Cl>CO.O1CCCC1>[NH2:8][CH2:9][C:10]1[CH:11]=[C:12]([C:18](=[O:20])[CH3:19])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 3922617HCID 3922617, compound

Product 1

HCID 19439680HCID 19439680, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Hydrazine hydrate (3.06 g) was added to a suspension of 3'-phthalimidomethyl-4'-methoxyacetophenone (15.74 g) in methanol (150 ml) and tetrahydrofuran (150 ml) at room temperature and the mixture was stirred at room temperature for 24 hours. Dilute hydrochloric acid (conc. hydrochloric acid (5 ml) in water (100 ml)) was added slowly to the mixture with cooling and the mixture was stirred at room temperature for 1 hour. The mixture was concentrated. Water (100 ml) was added thereto and the mixture was alkalized to pH 10 with 30% aqueous potassium carbonate solution and extracted with ethyl acetate (300 ml). The extract was dried with magnesium sulfate. The solvent was removed under reduced pressure to afford 3'-aminomethyl-4'-methoxyacetophenone (4.45 g).

Workup

  1. temperaturewith cooling
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. concentrationThe mixture was concentrated
  4. additionWater (100 ml) was added
  5. extractionextracted with ethyl acetate (300 ml)
  6. dry with materialThe extract was dried with magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-09db1c266b91498285a83bd0b0c0e292
Source dataset
uspto-grants-1996_07
Patent number
US05532258

Reaction notes

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