Tin tetrachloride → HCID 67575802, compound

HRID 925119Notes

Reaction equation

HRID 925119 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH2:11][C:12]#[N:13])=[C:5]([N+:14]([O-])=O)[CH:4]=1.[Sn](Cl)(Cl)(Cl)Cl>C(O)C>[CH3:10][O:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[N:14]=[C:12]([NH2:13])[CH2:11]2

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 2229922-(4,5-dimethoxy-2-nitrophenyl)acetonitrile

Product 1

HCID 67575802HCID 67575802, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile (0.22 g, 1 mmol) in ethanol (15 ml) was treated with tin chloride (0.50 g, 2.2 mmol) and heated to 70° C. for 72 hours. The reaction mixture was allowed to cool to room temperature, extracted with EtOAc and washed with 1N NaOH and water. The combined organic extracts were dried over MgSO4, filtered and concentrated. HPLC purification provided 5,6-dimethoxy-3H-indol-2-amine (12 mg, 6.2%). 1H NMR (400 MHz, DMSO) δ 11.82 (s, 1H), 9.80 (s, 1H), 9.54 (s, 1H), 7.11 (s, 1H), 6.82 (s, 1H), 4.10 (s, 2H), 3.77 (s, 3H), 3.73 (s, 3H). MS (APCI) m/z 193 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with EtOAc
  3. washwashed with 1N NaOH and water
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customHPLC purification

Sources & evidence

ORD record
ord-9a6841c10c324fa982a61336fdfcafb7
Source dataset
uspto-grants-2016_03
Patent number
US09284272B2

Reaction notes

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