Ammonia → HCID 59312283, compound

HRID 2077054Notes

Reaction equation

HRID 2077054 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]2[C:15](Cl)=[N:16][C:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)=[N:18][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N>O1CCCC1.[Zn]>[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[N:16][C:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)=[N:18][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 59312360HCID 59312360, compound

Product 1

HCID 59312283HCID 59312283, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Zinc dust (943 mg, 14.4 mmol) was added to a mixture of the product from Step B (221 mg, 0.56 mmol) and 0.880 ammonia (20 ml) in tetrahydrofuran (5 ml). This was heated to reflux for 5 h. The reaction mixture was filtered then filtrate was extracted with ethyl acetate (15 ml). The organic phase was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on a silica cartridge, eluting with DCM:MeOH (100:0 to 95:5), to afford the title compound as a pale orange oil in 66.9% yield, 135 mg.

Workup

  1. temperatureThis was heated
  2. temperatureto reflux for 5 h
  3. filtrationThe reaction mixture was filtered
  4. extractionfiltrate was extracted with ethyl acetate (15 ml)
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on a silica cartridge
  8. washeluting with DCM:MeOH (100:0 to 95:5)

Sources & evidence

ORD record
ord-4b70d11b7c804cc581b39dfa2745ddef
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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