Methane → HCID 43518115, compound

HRID 2064116Notes

Reaction equation

HRID 2064116 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[N+:17]([O-])=O)[CH:5]=[CH:6][CH:7]=1.C.O.NN>CO>[NH2:17][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:9]=1[NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:13]#[N:14]

Participants

5

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 67152351HCID 67152351, compound

Product 1

HCID 43518115HCID 43518115, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of compound C (1 g, 3.14 mmol) in methanol (10 mL) was added anhydrous FeCl3 (100 mg, 0.65 mmol) and charcoal (100 mg). The mixture was stirred at 60° C. and at that temperature hydrazine hydrate (10 mL) was added slowly where after the temperature was raised to 80° C. for 1.5 h. The reaction mixture was cooled to RT, filtered through a small pad of celite and washed with methanol. The organic layer was concentrated and washed with water, to give light brown solid D (200 mg, 22%).

Workup

  1. additionwas added slowly where after the temperature
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through a small pad of celite
  4. washwashed with methanol
  5. concentrationThe organic layer was concentrated
  6. washwashed with water
  7. customto give light brown solid D (200 mg, 22%)

Sources & evidence

ORD record
ord-c9a52fa1d8ce46f392b457c6832406c2
Source dataset
uspto-grants-2012_10
Patent number
US08288418B2

Reaction notes

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