Butyl nitrite → HCID 9880995, compound

HRID 2183542Notes

Reaction equation

HRID 2183542 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[NH2:24])[CH2:4][CH3:5])[CH3:2].[N:25](OCCCC)=O>C(#N)C>[CH2:1]([CH:3]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]2[N:14]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[N:25]=[N:24][C:8]=12)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 10996Butyl nitrite2×HCID 21912102HCID 21912102, compound

Product 1

HCID 9880995HCID 9880995, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4-(1-Ethyl-propoxy)-6-methyl-N2-(2,4,6-trimethyl-phenyl)-pyridine-2,3-diamine (50 mg, 0.153 mmol) and butyl nitrite (24 mg, 0.229 mmol) in 4 ml acetonitrile was heated at 65° C. for 2 hours. An additional 0.13 ml of butyl nitrite was added and the resulting mixture was heated at 65° C. for 2 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 58 mg of brown oil. The oil was purified through silica gel column chromatography using 5% ethyl acetate in hexane as eluent to give 46 mg (88%) of the title compound as a light yellow oil. 1H NMR (CDCl3) ä 7.04(s, 2H), 6.60(s, 1H), 5.26(m, 1H), 2.57(s, 3H), 2.38(s, 3H), 1.94(s, 6H), 1.8-2.0(m, 4H), 1.07(t, 6H) ppm.

Workup

  1. temperaturethe resulting mixture was heated at 65° C. for 2 hours
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd211d42e0784aa7aa11959bfc7b74c3
Source dataset
uspto-grants-2005_05
Patent number
US06900217B2

Reaction notes

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