2-Chloro-6-(1H-pyrrol-1-yl)benzonitrile → [2-chloro-6-(1H-pyrrol-1-yl)phenyl]methanamine

HRID 1161638Notes

Reaction equation

HRID 1161638 reaction equation
[Cl:1][C:2]1[C:3]([C:13]#[N:14])=[C:4]([N:8]2[CH:12]=[CH:11][CH:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[NH2:14][CH2:13][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1

Participants

4

Reactant 2

HCID 6087322-Chloro-6-(1H-pyrrol-1-yl)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 3559150[2-chloro-6-(1H-pyrrol-1-yl)phenyl]methanamineYield 92.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-(3′chloro-2′-cyanophenyl)pyrrole (10 g) in diethyl ether solution was added dropwise to a solution of 1M lithium aluminium hydride in ether solution (100 ml) under nitrogen gas. After addition was complete, the reaction mixture was refluxed for 2 h. and then allowed to stir at room temperature overnight (18 h). The mixture was subsequently quenched with water (4 ml), 2N NaOH (8 ml) and water (16 ml). Stirring was continued for a further 1 h after addition. The crystalline salts were filtered and the filtrate dried over anhydrous magnesium sulphate. After filtering, the ether filtrate was evaporated in vacuo to give the title compound (9.4 g) as a colourless oil.

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was refluxed for 2 h.
  3. customThe mixture was subsequently quenched with water (4 ml), 2N NaOH (8 ml) and water (16 ml)
  4. stirringStirring
  5. waitwas continued for a further 1 h
  6. additionafter addition
  7. filtrationThe crystalline salts were filtered
  8. dry with materialthe filtrate dried over anhydrous magnesium sulphate
  9. filtrationAfter filtering
  10. customthe ether filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-7a8bb61c2b11475893fa8f1fa7aefaca
Source dataset
uspto-grants-2010_10
Patent number
US07820650B2

Reaction notes

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