Hydrochloric Acid → Ethyl 2-amino-5-fluoro-2,3-dihydro-1H-indene-2-carboxylate

HRID 1047676Notes

Reaction equation

HRID 1047676 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1([N+:17]#[C-])[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:16])[CH:13]=2)[CH2:8]1)=[O:6])[CH3:3].C([O-])(O)=O.[Na+]>>[CH2:2]([O:4][C:5]([C:7]1([NH2:17])[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:16])[CH:13]=2)[CH2:8]1)=[O:6])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 593143475-Fluoro-2-isocyano-indan-2-carboxilic acid ethyl ester

Product 1

HCID 59314154Ethyl 2-amino-5-fluoro-2,3-dihydro-1H-indene-2-carboxylate

Procedure

A methanolic solution of conc. HCl (35%) (9.3 mL in 110 mL of MeOH) is added dropwise to a methanolic solution of 5-fluoro-2-isocyano-indan-2-carboxilic acid ethyl ester E (17.6 g, 75.4 mmol) at RT and the mixture is stirred for 2 h. The mixture is then neutralized by saturated NaHCO3 solution and extracted with DCM (500 mL). The organic layer is washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure to obtain 16.0 g (94%) of F as yellowish semi solid.

Workup

  1. extractionextracted with DCM (500 mL)
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto obtain 16.0 g (94%) of F as yellowish semi solid

Sources & evidence

ORD record
ord-10b648c714754b6ca86e1b3fcbcf6251
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…