Hydrochloric Acid → Hydrochloric Acid

HRID 1802351Notes

Reaction equation

HRID 1802351 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH2:11][CH3:12])[C:6]#[N:7].[H-].[H-].[H-].[H-].[Li+].[Al+3].[ClH:19].CCOCC>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH2:11][CH3:12])[CH2:6][NH2:7].[ClH:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 574847153-Methoxy-4-ethyl-benzonitrile

Product 2

HCID 313Hydrochloric AcidHCID 574847143-Methoxy-4-ethylbenzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-methoxy-4-ethyl-benzonitrile (7-2, 1.5 g, 9.31 mmol) in THF (45 mL) at 0° C. was added LAH (40 mL, 40.0 mmol, 1M in THF) and stirred at 0° C. for 0.5 h. Quenched carefully over a period of 0.5 h with EtOAc at 0° C. and stirred for 15 minutes. Following this, water (1.5 mL) was added to this mixture and stirred for 15 minutes followed by 15% NaOH (1.5 mL) and again stirred for 15 minutes. Lastly, water (4.5 mL) was added and stirred for 15 more minutes. The mixture was dried over Mg2SO4, filtered and concentrated to yield a clear semi-solid. This semi-solid was treated with 2.0M HCl in ether (4.65 mL, 9.3 mmol) and the reaction contents were concentrated to afford the desired product as a white powder (7-3) in the form of a mono HCl salt. ESI+MS [M+H]+ C8H12N2O2: M-16 (—NH2), 149.1 found, 149.2 required.

Workup

  1. customQuenched carefully over a period of 0.5 h with EtOAc at 0° C.
  2. stirringstirred for 15 minutes
  3. additionwas added to this mixture
  4. stirringstirred for 15 minutes
  5. stirringagain stirred for 15 minutes
  6. additionLastly, water (4.5 mL) was added
  7. stirringstirred for 15 more minutes
  8. dry with materialThe mixture was dried over Mg2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto yield a clear semi-solid
  12. customthe reaction contents
  13. concentrationwere concentrated

Sources & evidence

ORD record
ord-777aa7098daa417b8fbb52626ebe870c
Source dataset
uspto-grants-2013_01
Patent number
US08349872B2

Reaction notes

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