N,N-Diethylaniline → HCID 58071863, compound

HRID 715704Notes

Reaction equation

HRID 715704 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][CH:19]=[N:20]3)=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:36])=O>COC(C)(C)C>[Cl:36][C:15]1[N:14]=[C:13]([C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 66713311HCID 66713311, compound

Product 1

HCID 58071863HCID 58071863, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

565 mg 7-(3,4,5-Trimethoxy-phenyl)-[1,6]-naphthyridine (5.2) and 15 μL N,N-diethylaniline were stirred into 4 mL phosphorus oxychloride overnight at 100° C. and at ambient temperature over 2 days. The reaction mixture was evaporated down, and a small amount of ethyl acetate was added. Upon scratching a precipitate were formed. Methyl-tert-butylether was added and the precipitate was isolated and dried overnight at 50° C. under vacuo.

Workup

  1. customThe reaction mixture was evaporated down
  2. additiona small amount of ethyl acetate was added
  3. customwere formed
  4. customthe precipitate was isolated
  5. customdried overnight at 50° C. under vacuo

Sources & evidence

ORD record
ord-420d9f40fb294f939d06f87be2f7d3db
Source dataset
uspto-grants-2015_11
Patent number
US09187478B2

Reaction notes

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