Hydrochloric Acid → 6-Fluoro-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 988972Notes

Reaction equation

HRID 988972 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6][CH2:5]2.C([O-])(=O)C.[NH4+].[BH3-]C#[N:20].[Na+].Cl>C1COCC1.CO>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([NH2:20])[CH2:6][CH2:5]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 149151166-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 162443376-Fluoro-1,2,3,4-tetrahydronaphthalen-2-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Over a solution of 6-fluorotetralone (6-fluoro-3,4-dihydro-1 H-naphthalen-2-one; 1 equivalent) and ammonium acetate (5 equivalents) in a 2:1 mixture of MeOH:THF (0.24 M), was carefully added NaCNBH3 (2 eq), and the reaction mixture was stirred at room temperature for 2 hours. Concentrated HCl was added at 0° C. until the pH was less than 2, and the MeOH was removed in vacuo. The residue was taken up in water and extracted with CHCl3 (2×). The aqueous solution was basified with solid KOH and extracted with CHCl3 (3×). The combined extracts were dried (MgSO4) and evaporated in vacuo to give the titled compound.

Workup

  1. customthe MeOH was removed in vacuo
  2. extractionextracted with CHCl3 (2×)
  3. extractionextracted with CHCl3 (3×)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-396b1468175f47059e069502df5eca4d
Source dataset
uspto-grants-2003_10
Patent number
US06638927B2

Reaction notes

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