Sodium Hydroxide → 2-Methylquinolin-3-amine

HRID 2281122Notes

Reaction equation

HRID 2281122 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.O.O.[Sn](Cl)Cl.[OH-].[Na+]>Cl.O>[NH2:12][C:11]1[C:2]([CH3:1])=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 125950392-Methyl-3-nitroquinoline

Product 1

HCID 123006962-Methylquinolin-3-amine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-methyl-3-nitroquinoline (400 mg, 2.13 mmol) in conc. HCl (8 mL) was heated to 50° C. Tin (II) chloride dihydrate (1.2 g, 5.3 mmol) was added. The mixture was stirred at 50° C. overnight. The mixture was diluted with water (20 mL). The pH was brought to 9 by addition of aqueous 5 N NaOH. The mixture was cooled to 4° C. and extracted with ethyl acetate (2×30 mL). The combined extracts were washed with ice-cold water (40 mL) and dried over anhydrous Na2SO4, filtered, and concentrated to give 3-amino-2-methylquinoine (270 mg, 80%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.84 (d, J=8.4 Hz, 1H), 7.51 (dd, J=1.2, 8.0 Hz, 1H), 7.39-7.30 (m, 2H), 7.16 (s, 1H), 3.77 (s, 2H), 2.56 (s, 3H).

Workup

  1. temperatureThe mixture was cooled to 4° C.
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. washThe combined extracts were washed with ice-cold water (40 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 3-amino-2-methylquinoine (270 mg, 80%) as a yellow solid

Sources & evidence

ORD record
ord-19931c93b48640439b0d14057e4f0df8
Source dataset
uspto-grants-2015_09
Patent number
US09139538B2

Reaction notes

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