Ethanol → (R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 1161263Notes

Reaction equation

HRID 1161263 reaction equation
[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:18]([O-])=O)[C:9]1=[O:21])[CH3:7])(=[O:3])[CH3:2].C(O)C.[Cl-].[NH4+].O>[Fe]>[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[NH2:18])[C:9]1=[O:21])[CH3:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 59515745(R)-2-(5-Nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 59515825(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
85 °C

Procedure

To a suspension of (R)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate (5.34 g, 0.0184 mol) in ethanol (100 mL, 2 mol) was added ammonium chloride (9.840 g, 0.1840 mol) in water (100 mL, 6 mol). The reaction heated at 85° C. and iron (4.11 g, 0.0736 mol) was added in four portions 3 minutes apart. The reaction started turning dark and became completely brown. After 2 hours, the flask was removed from the oil bath and 150 ml of ethyl acetate was added in the flask. The organic layer was decanted and the aqueous layer was extracted again with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give a bright yellow oil.

Workup

  1. customthe flask was removed from the oil bath and 150 ml of ethyl acetate
  2. additionwas added in the flask
  3. customThe organic layer was decanted
  4. extractionthe aqueous layer was extracted again with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a bright yellow oil

Sources & evidence

ORD record
ord-5303d4781d894b2eaeb4e0417e554603
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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