1,1-Dimethoxyethyl(dimethyl)amine → HCID 18765287, compound

HRID 480576Notes

Reaction equation

HRID 480576 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[C:7]([CH3:12])[CH:6]=[CH:5][N:4]=1.CO[C:15](OC)(N(C)C)[CH3:16]>>[CH3:15][C:16]1[NH:9][C:8]2[C:7]([CH:12]=1)=[CH:6][CH:5]=[N:4][C:3]=2[O:2][CH3:1]

Participants

3

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 109866452-methoxy-3-nitro-4-picoline

Product 1

HCID 18765287HCID 18765287, compoundYield 57%

Procedure

2-Methoxy-3-nitro-4-methyl pyridine (200 mg, 1.2 mmol) and dimethylacetamide dimethylacetal (0.5 mL) were heated at 130° C. for 18 h. The reaction mixture was cooled and concentrated in vacuo to a deep purple-red oil. Benzene (4 mL) and 10% Pd/C (25 mg) were added and the solution hydrogenated at 45 psi for 18 h (Parr apparatus). The red coloration disappeared. The crude reaction mixture was purified directly by silica gel chromatography (20% EtOAc/hex) to furnish 2-methyl-7-methoxy-6-azaindole (112 mg, 57% yield). LC-MS 163.1, M+H.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo to a deep purple-red oil
  3. additionBenzene (4 mL) and 10% Pd/C (25 mg) were added
  4. customThe crude reaction mixture
  5. customwas purified directly by silica gel chromatography (20% EtOAc/hex)

Sources & evidence

ORD record
ord-0fd2aa13b7f64369b7441b5594dd5816
Source dataset
uspto-grants-2003_11
Patent number
US06653304B2

Reaction notes

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