Benzylamine → HCID 22172694, compound

HRID 1168382Notes

Reaction equation

HRID 1168382 reaction equation
P(Cl)(Cl)(Cl)=O.[N+:6]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1O)=[N:16][CH:15]=[CH:14][CH:13]=2)([O-:8])=[O:7].C(N(C(C)C)CC)(C)C.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C=O.O>[C:30]1([CH2:29][NH:36][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[N:11]=[CH:10][C:9]=2[N+:6]([O-:8])=[O:7])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178526774HCID 178526774, compound

Product 1

HCID 22172694HCID 22172694, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Phosphorus oxychloride (3.5 mL, 37.7 mmol) was reacted with N,N-dimethylformamide (15 mL) while chilling in an ice bath. This mixture was added to a solution of 3-nitro[1,5]naphthyridin-4-ol (6.0 g, 31.4 mmol) in N,N-dimethylformamide (60 mL). The reaction mixture was warmed in an oil bath to 60° C. After 3 hours the reaction mixture was poured into ice water. The resulting precipitate was isolated by filtration and then washed with water. The wet crude 5-chloro-3-nitro[1,5]naphthyridine was suspended in dichloromethane (150 mL). Diisopropylethylamine (1.2 eq) was added followed by the slow addition of benzylamine (4.7 mL g, 40 mmol). The reaction mixture was refluxed for 2 hours and then combined with water (˜100 mL). The layers were separated and the organic layer was concentrated under vacuum to provide 5.5 g of N-phenylmethyl-3-nitro[1,5]naphthyridin-4-amine. A small sample was recrystallized from isopropanol to provide a pure sample, m.p. 127-129° C. Analysis: Calculated for C15H12N4O2: %C, 64.28; %H, 4.32; %N, 19.99; Found: %C, 63.89; %H, 4.40: %N, 20.35.

Workup

  1. temperaturewhile chilling in an ice bath
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with water
  4. temperatureThe reaction mixture was refluxed for 2 hours
  5. customThe layers were separated
  6. concentrationthe organic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-4db73e616f564f7e9847d508b3bc9308
Source dataset
uspto-grants-2003_09
Patent number
US06624172B2

Reaction notes

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