Sodium Hydroxide → HCID 20619502, compound

HRID 868994Notes

Reaction equation

HRID 868994 reaction equation
C([NH:8][C:9]1[C:10]2[CH:11]=[CH:12][C:13]([CH3:19])=[N:14][C:15]=2[CH:16]=[CH:17][N:18]=1)C1C=CC=CC=1.[OH-].[Na+]>S(=O)(=O)(O)O.O>[CH3:19][C:13]1[CH:12]=[CH:11][C:10]2[C:9]([NH2:8])=[N:18][CH:17]=[CH:16][C:15]=2[N:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70113511HCID 70113511, compound

Product 1

HCID 20619502HCID 20619502, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
130 °C

Procedure

N-Benzyl-2-methyl-1,6-naphthyridin-5-amine (1.42 g, 5.7 mmol) was dissolved in sulfuric acid (6 mL) and water (3 mL). The solution was heated to 130° C. and stirred for 3 hours. The reaction mixture was poured into ice water and neutralized with sodium hydroxide adjusting pH to 8-10. The solution was then concentrated under reduced pressure. The solid was triturated in ethanol (30 mL×2) and filtered. The filtrate was concentrated to dryness and purified by reverse phase column chromatography, and a brown solid (485 mg) was obtained. MS (ESI): m/z 160 [M+H]+.

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. customThe solid was triturated in ethanol (30 mL×2)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to dryness
  5. custompurified by reverse phase column chromatography

Sources & evidence

ORD record
ord-69e4e57a20774509b9b199cddcf3dca0
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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