Methanol → 3-methoxy-N1-(3-methoxypropyl)benzene-1,2-diamine

HRID 1096626Notes

Reaction equation

HRID 1096626 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:15]([O-])=O)=[C:5]([CH:12]=[CH:13][CH:14]=1)[NH:6][CH2:7][CH2:8][CH2:9][O:10][CH3:11].CO>[Zn].C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][CH:12]=[C:5]([NH:6][CH2:7][CH2:8][CH2:9][O:10][CH3:11])[C:4]=1[NH2:15]

Participants

5

Reactant 2

HCID 887MethanolHCID 667850723-methoxy-N-(3-methoxypropyl)-2-nitroaniline

Product 1

HCID 667862403-methoxy-N1-(3-methoxypropyl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Into a 100 mL round bottomed flask was added 3-methoxy-N-(3-methoxypropyl)-2-nitroaniline (36A) (560 mg, 2.33 mmol) and methanol (46 mL). Zinc metal (2.11 g, 32.4 mmol) and acetic acid (2.0 mL) was added and the mixture was stirred at room temperature for 5 hr. The mixture was filtered through a fritted Buchner funnel and the solvent was removed under vacuum. Ethyl acetate (100 mL) was added and the precipitate was filtered through a Buchner funnel with a pad of Celite. The filtrate was concentrated under vacuum to leave 3-methoxy-N1-(3-methoxypropyl)benzene-1,2-diamine (37B) as a yellow oil which was used without further purification. ESI-MS:mlz 211.4 (M-F1-1)+.

Workup

  1. filtrationThe mixture was filtered through a fritted Buchner funnel
  2. customthe solvent was removed under vacuum
  3. additionEthyl acetate (100 mL) was added
  4. filtrationthe precipitate was filtered through a Buchner funnel with a pad of Celite
  5. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-a8267ede6e3f4da99bb01b9fd023a216
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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