3-bromo-N-cyclopropyl-5-nitropyridin-4-amine → 5-Bromo-N~4~-cyclopropylpyridine-3,4-diamine

HRID 1394196Notes

Reaction equation

HRID 1394196 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:12]([O-])=O)[C:7]=1[NH:8][CH:9]1[CH2:11][CH2:10]1>C(O)(=O)C.[Fe]>[Br:1][C:2]1[C:7]([NH:8][CH:9]2[CH2:11][CH2:10]2)=[C:6]([NH2:12])[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 1

HCID 249036703-bromo-N-cyclopropyl-5-nitropyridin-4-amine

Product 1

HCID 249036715-Bromo-N~4~-cyclopropylpyridine-3,4-diamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of the product obtained from Step 3 (2.95 g, 11.4 mmol) in glacial acetic acid (50 ml) was added iron dust (3.35 g, 60 mmol). The resulting mixture was stirred at 80° C. for 90 minutes, after which it was filtered through Celite and the liquor concentrated under vacuum. The crude product was re-dissolved in ethyl acetate, basified with sodium bicarbonate and refiltered. Th organic phase was washed with water three times, followed by twice with brine before concentrating under vacuum to give the product. Passed through a silica plug affording product as an oil, 1.65 g (63%); MS (ES+) m/e 228/230 [M+H]+.

Workup

  1. filtrationafter which it was filtered through Celite
  2. concentrationthe liquor concentrated under vacuum
  3. dissolutionThe crude product was re-dissolved in ethyl acetate
  4. washTh organic phase was washed with water three times
  5. concentrationbefore concentrating under vacuum
  6. customto give the product
  7. customaffording product as an oil, 1.65 g (63%)

Sources & evidence

ORD record
ord-f2cf3318c4c54641bba99b24e8a05e1c
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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