Ethanol → HCID 57990560, compound

HRID 1625007Notes

Reaction equation

HRID 1625007 reaction equation
[CH:1]1([N:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[N+:14]([O-])=O)[C:5]2=[O:17])[CH2:3][CH2:2]1.C(O)C.[Cl-].[NH4+].O>[Fe]>[NH2:14][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:12]=[CH:13][N:4]([CH:1]1[CH2:3][CH2:2]1)[C:5]2=[O:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 57990527HCID 57990527, compound

Product 1

HCID 57990560HCID 57990560, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
85 °C

Procedure

To a suspension of 2-cyclopropyl-5-nitro-2H-isoquinolin-1-one (3.7 g, 0.015 mol) in Ethanol (80 mL, 1 mol) was added ammonium chloride (8 g, 0.2 mol) in Water (80 mL, 4 mol) and the reaction heated at 85° C. and then iron (4 g, 0.06 mol) was added. The reaction started turning dark and became completely brown. The reaction was heated for 1 h. LC/MS showed no starting material left and only one peak which to give the desired MW. The reaction was removed from the oil bath and 150 ml of methylene chloride was added in the flask. The mixture layers were separated and aqueous layer was extracted with CH2Cl2 (100 mL×3). The combined organic layers were washed once with brine. The organic layer was collected, dried over Na2SO4 and reduced in vacuo to produce a yellow-orange solid.

Workup

  1. temperatureThe reaction was heated for 1 h
  2. waitleft
  3. customonly one peak which to give the desired MW
  4. customThe reaction was removed from the oil bath and 150 ml of methylene chloride
  5. additionwas added in the flask
  6. customThe mixture layers were separated
  7. extractionaqueous layer was extracted with CH2Cl2 (100 mL×3)
  8. washThe combined organic layers were washed once with brine
  9. customThe organic layer was collected
  10. dry with materialdried over Na2SO4
  11. customto produce a yellow-orange solid

Sources & evidence

ORD record
ord-482c63839298498f888053388f261a76
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

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