Water → N-(2-hydroxy-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine

HRID 547333Notes

Reaction equation

HRID 547333 reaction equation
[NH2:1][CH:2](C)[CH:3]([CH3:5])[OH:4].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[N:11]=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19].[CH2:21](N(CC)CC)C.O>ClCCl>[OH:4][C:3]([CH3:5])([CH3:21])[CH2:2][NH:1][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[N:11]=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2268313-Aminobutan-2-olHCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Product 1

HCID 22172695N-(2-hydroxy-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amineYield 59.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere 2-amino-1-methylpropan-1-ol (25.5 g, 0.28 mol) was added over a period of 30 minutes to a chilled (15° C.) solution of 4-chloro-3-nitro[1,5]naphthyridine (54.5 g, 0.26 mol) and triethylamine (39.5 g, 0.39 mol) in dichloromethane (1 L). The temperature of the reaction mixture was maintained below about 30° during the addition. After the addition was complete the reaction mixture was stirred at ambient temperature overnight. The resulting precipitate was isolated by filtration, slurried with water, and again isolated by filtration to provide 40.53 g of N-(2-hydroxy-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine as a yellow solid.

Workup

  1. temperatureThe temperature of the reaction mixture was maintained below about 30° during the addition
  2. additionAfter the addition
  3. customThe resulting precipitate was isolated by filtration
  4. customagain isolated by filtration

Sources & evidence

ORD record
ord-05550b88923941d69ebb37a530ef3c38
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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