Ammonium Chloride → 4-(4-Amino-thiophen-2-ylmethyl)-2H-phthalazin-1-one

HRID 600270Notes

Reaction equation

HRID 600270 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[NH:12][N:11]=2)[S:7][CH:8]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[NH:12][N:11]=2)[S:7][CH:8]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 598565794-(4-Nitro-thiophen-2-ylmethyl)-2H-phthalazin-1-one

Product 1

HCID 598565584-(4-Amino-thiophen-2-ylmethyl)-2H-phthalazin-1-one

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-(4-nitro-thiophen-2-ylmethyl)-2H-phthalazin-1-one (27) (0.90 g, 5.71 mmol) in ethanol (25 mL) under a nitrogen blanket was added dropwise a solution of ammonium chloride (0.31 g, 5.7 mmol) in water 18 mL). After stirring the resultant solution for 5 minutes, iron powder (0.64 g, 11.5 mmol) was added in one portion. The yellow mixture was stirred at 80° C. for 3 hours. The reaction mixture was filtered hot through celite which was washed with ethyl acetate (80 mL). The concentrated in vacuo and then diluted with ethyl acetate (20 mL) washed with brine (20 mL), dried over magnesium, sulphate and dried in vacuo to afford the title cpd as a bright yellow powder. Single peak in LC-MS analysis, (0.68 g, 84% purity and required no further purification; m/z (LC-MS, ESP), RT=2.94 (M+H) 258.

Workup

  1. filtrationThe reaction mixture was filtered hot through celite which
  2. washwas washed with ethyl acetate (80 mL)
  3. concentrationThe concentrated in vacuo
  4. additiondiluted with ethyl acetate (20 mL)
  5. washwashed with brine (20 mL)
  6. dry with materialdried over magnesium, sulphate
  7. customdried in vacuo
  8. customto afford the title cpd as a bright yellow powder
  9. customno further purification
  10. customm/z (LC-MS, ESP), RT=2.94 (M+H) 258

Sources & evidence

ORD record
ord-84f76ef90b654fa28d564bf8069a1a67
Source dataset
uspto-grants-2011_03
Patent number
US07902193B2

Reaction notes

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