Toluene → HCID 18317237, compound

HRID 1700128Notes

Reaction equation

HRID 1700128 reaction equation
[NH2:1][NH2:2].[N:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=2)[CH2:11][C:12](=O)[CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.C1(C)C=CC=CC=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>CCO>[N:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:1]=[N:2][C:12]([CH:13]3[CH2:14][CH2:15][N:16]([C:19]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[O:20])[CH2:17][CH2:18]3)=[CH:11][C:10]=2[C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:38])([F:37])[F:39])[CH:31]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 9321HydrazineHCID 18317247HCID 18317247, compound

Product 1

HCID 18317237HCID 18317237, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under Ar, hydrazine (0.5 mL, 0.51 g, 15.9 mmol) was added to a solution of 34 (3.3 g) in EtOH (75 mL). After 4 h, the solution was concentrated to dryness and the residue treated with toluene (60 mL) dioxane (60 mL) and DDQ (0.8 g, 3.5 mmol). After 15 h, the reaction was concentrated to dryness. The residue was chromatographed on a Still column (50 mm) and the product eluted with 100% EtOAc to yield 1.2 g of 35.

Workup

  1. concentrationthe solution was concentrated to dryness
  2. waitAfter 15 h
  3. concentrationthe reaction was concentrated to dryness
  4. customThe residue was chromatographed on a Still column (50 mm)
  5. washthe product eluted with 100% EtOAc

Sources & evidence

ORD record
ord-6247a9b786734c9abc34b43c92496952
Source dataset
uspto-grants-2002_02
Patent number
US06350744B1

Reaction notes

Loading…