Toluene → N4-Isobutyl-1,5-naphthyridine-3,4-diamine

HRID 2090171Notes

Reaction equation

HRID 2090171 reaction equation
[CH3:1][CH:2]([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[N:8]=[CH:7][C:6]=1[N+:15]([O-])=O.C1(C)C=CC=CC=1>[Pt].C(O)(C)C>[CH3:1][CH:2]([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15]

Participants

5

Reactant 2

HCID 1140TolueneHCID 54184816N-(2-Methylpropyl)-3-nitro-1,5-naphthyridin-4-amine

Product 1

HCID 53699038N4-Isobutyl-1,5-naphthyridine-3,4-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
22 °C

Procedure

A hydrogenation vessel was charged with N4-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine (7.50 kg, 30.5 mol) and toluene (125.0 kg). A suspension of 3% platinum on carbon (0.44 kg, approximately 33% by weight (w/w) in water) in isopropanol (7.0 kg) was added to the vessel followed by a rinse with toluene (10.0 kg). The reaction mixture was then placed under hydrogen pressure (2.4×105 Pa, 2.4 bars) for six hours while stirring and maintaining the temperature at 22° C. The reaction mixture was then filtered, and the filter cake was washed with toluene (30.0 kg). The filtrate was concentrated under reduced pressure (1×104 Pa, 0.1 bar) at approximately 50° C. to provide a solution of N4-(2-methylpropyl)[1,5]naphthyridine-3,4-diamine in toluene (75 L, approximately 10 mL/g).

Workup

  1. additionwas added to the vessel
  2. washa rinse with toluene (10.0 kg)
  3. customfor six hours
  4. filtrationThe reaction mixture was then filtered
  5. washthe filter cake was washed with toluene (30.0 kg)
  6. concentrationThe filtrate was concentrated under reduced pressure (1×104 Pa, 0.1 bar) at approximately 50° C.

Sources & evidence

ORD record
ord-c8ffe811e569428abc65b2939153c83f
Source dataset
uspto-grants-2013_05
Patent number
US08436176B2

Reaction notes

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