HCID 21914164, compound → HCID 57436580, compound

HRID 730930Notes

Reaction equation

HRID 730930 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=2[O:18][CH3:19])[CH:6]=[CH:7][CH:8]=1)#[N:2]>C1COCC1.ClCCl>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=2[O:18][CH3:19])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 21914164HCID 21914164, compound

Product 1

HCID 57436580HCID 57436580, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(3-cyanophenyl)-4-nitroanisole (8.0 g) from Example 111, part a, was dissolved in THF (200 mL) and purged with nitrogen. A 11.0M solution of borane in THF (135 mL) was then added, and the reaction was heated at reflux for 4 hours. When the reaction was complete, the mixture was cooled to room temperature and 4.0N HCl in dioxane (25 mL) was added dropwise over 30 minutes. Methanol (200 mL) was slowly added to the acidified solution, and the solvent was removed in vacuo. The resulting gum was redissolved in methanol (150 mL) and concentrated in vacuo to give a solid. The product was dissolved in dichloromethane (150 mL) and cooled to −20° C. to give 2-(3-aminomethylphenyl)-4-nitroanisole which was collected on a filter and dried in vacuo.

Workup

  1. custompurged with nitrogen
  2. additionA 11.0M solution of borane in THF (135 mL) was then added
  3. temperaturethe reaction was heated
  4. temperatureat reflux for 4 hours
  5. addition4.0N HCl in dioxane (25 mL) was added dropwise over 30 minutes
  6. additionMethanol (200 mL) was slowly added to the acidified solution
  7. customthe solvent was removed in vacuo
  8. dissolutionThe resulting gum was redissolved in methanol (150 mL)
  9. concentrationconcentrated in vacuo
  10. customto give a solid
  11. temperaturecooled to −20° C.

Sources & evidence

ORD record
ord-6a567da226074b3fbbec6eee99140885
Source dataset
uspto-grants-2009_09
Patent number
US07582765B2

Reaction notes

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