Ammonia → HCID 59004663, compound

HRID 1668458Notes

Reaction equation

HRID 1668458 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([N+:19]([O-])=O)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.O.NN.N.C(Cl)Cl>CO.[Ni]>[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 59004644HCID 59004644, compound

Product 1

HCID 59004663HCID 59004663, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

A solution of compound 60 (400 mg, 1.4 mmol) in methanol (10 mL) was added to Raney Nickel (slurry in H2O, 50 mg) in a round bottom flask. The suspension was treated with hydrazine hydrate (435 μL, 14.0 mmol) and heated at reflux for 10 minutes then filtered through a pad of celite. The celite pad washed with methanol (10 mL). The filtrate was concentrated to give a dark brown residue which was subjected to flash silica gel chromatography (2M NH3 in MeOH:CH2Cl2, 5:95) to give compound 61 (260 mg, 72.2%) as a viscous oil. 1H NMR (DMSO-d6) δ 7.14 (d, J=3.0 Hz, 1H), 7.09 (d, J=8.4 Hz, 1H), 6.67 (d, J=1.8 Hz, 1H), 6.52 (dd, J=1.8, 8.7 Hz, 1H), 6.09 (d, J=1.8 Hz, 1H), 4.45 (brs, 2H), 4.04 (t, J=7.2 Hz, 2H), 2.76-2.72 (m, 1H), 2.15 (s, 3H), 2.02-1.17 (m, 10H); ESI-MS (m/z, %): 258 (M+1).

Workup

  1. temperatureheated
  2. temperatureat reflux for 10 minutes
  3. filtrationthen filtered through a pad of celite
  4. washThe celite pad washed with methanol (10 mL)
  5. concentrationThe filtrate was concentrated
  6. customto give a dark brown residue which

Sources & evidence

ORD record
ord-0bcaeb12475c4eacbb89710b04e9d747
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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