Hydrochloric Acid → HCID 89704912, compound

HRID 1481363Notes

Reaction equation

HRID 1481363 reaction equation
[Li+].[BH4-].C[O:4][C:5](=O)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[C:13]#[N:14].Cl>C1COCC1.[Cl-].[Cl-].[Zn+2]>[NH2:14][CH2:13][C:7]1[C:8]([Cl:12])=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][OH:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 552646011211594-32-9

Product 1

HCID 89704912HCID 89704912, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a slurry of ZnCl2 (0.77 mmol) in 5 mL THF was added LiBH4 (1.64 mmol, 2M in THF) at RT. After heating to 50° C. for 90 min, a solution of 3-chloro-2-cyanobenzoic acid methyl ester (0.81 mmol) in 5 mL THF was slowly added and the mixture was heated to 60° C. overnight. The reaction mixture was then cooled to 5° C., acidified with 2M HCl solution and extracted with EtOAc. The aq. phase was basified with 1M NaOH solution, extracted twice with EtOAc, dried over MgSO4 and concentrated in vacuo to give the desired product as yellowish oil.

Workup

  1. temperaturethe mixture was heated to 60° C. overnight
  2. temperatureThe reaction mixture was then cooled to 5° C.
  3. extractionextracted with EtOAc
  4. extractionextracted twice with EtOAc
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89f513d18fba4aaa9c81694c59f705b1
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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