Hydrochloric Acid → Methyl 4-(2-aminoethoxy)benzoate

HRID 583674Notes

Reaction equation

HRID 583674 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)C(=O)C2=CC=CC=C12.NN.Cl>CO>[NH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 7679064Methyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)benzoate

Product 1

HCID 14097616Methyl 4-(2-aminoethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

19-2 (1.59 g, 4.89 mmol) was suspended in 25 mL MeOH. Upon addition of hydrazine (2.0 mL, 64 mmol) the reaction became homogeneous. After 20 h a heavy precipitate had formed. The pH was adjusted to 1 by addition of 6N HCl, MeOH evaporated, and the solid suspended in 1N HCl. After filtering through Celite, the filtrate was washed with CH2Cl2, the pH was adjusted to 12 with 6N NaOH. The aqueous layer was extracted with fresh CH2Cl2. This organic phase was dried (Na2SO4) and concentrated providing 19-3 as a white solid.

Workup

  1. customAfter 20 h a heavy precipitate had formed
  2. customevaporated
  3. filtrationAfter filtering through Celite
  4. washthe filtrate was washed with CH2Cl2
  5. extractionThe aqueous layer was extracted with fresh CH2Cl2
  6. dry with materialThis organic phase was dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ec48a48efae34717823a739ab5194fd2
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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