Hydrochloric Acid → 1,6-Naphthyridin-5-amine

HRID 1615695Notes

Reaction equation

HRID 1615695 reaction equation
[N:1]([C:4]1[N:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)=[N+]=[N-].Cl.[OH-].[Na+]>CO.CCOC(C)=O>[N:9]1[C:10]2[CH:11]=[CH:12][N:13]=[C:4]([NH2:1])[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866678085-Azido-1,6-naphthyridine

Product 1

HCID 292496221,6-Naphthyridin-5-amineYield 69.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of 5-azido-1,6-naphthyridine (3.4 g, 19.9 mmol) in MeOH (40 mL) was added hydrochloric acid (30 mL). Stannous chloride dihydrate (22.5 g, 99.5 mmol) was added. The mixture was stirred at 75° C. for 3.5 h. A yellow precipitate was formed. The mixture was filtered to give a yellow solid. The solid was suspended in EtOAc (200 mL). NaOH (saturated aqueous solution) was added to adjust pH to 9. A white precipitate was formed. The mixture was filtered and the filtrate was extracted with EtOAc (200 mL×6). The organic phase was dried over sodium sulfate and concentrated under reduced pressure to give 2.0 g of the crude product as a yellow solid. ESI MS: m/z 146 [M+H]+.

Workup

  1. customA yellow precipitate was formed
  2. filtrationThe mixture was filtered
  3. customto give a yellow solid
  4. customA white precipitate was formed
  5. filtrationThe mixture was filtered
  6. extractionthe filtrate was extracted with EtOAc (200 mL×6)
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c520df8822f4ac39fc03290dce236af
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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