5,6,7,8-Tetrahydroquinoline → 5,6,7,8-Tetrahydro-quinoline-8-carbonitrile

HRID 371182Notes

Reaction equation

HRID 371182 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH:16]([N:19](C(C)C)C#N)(C)C>C1C=CC=CC=1.CCCCCC>[C:16]([CH:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)#[N:19]

Participants

6

Reactant 3

HCID 663355,6,7,8-TetrahydroquinolineHCID 76520DiisopropylcyanamideHCID 178418339Butyllithium

Product 1

HCID 122789815,6,7,8-Tetrahydro-quinoline-8-carbonitrileYield 71%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 5,6,7,8-tetrahydroquinoline (6.5 ml, 50 mM) in benzene (35 ml) maintained below 10° was treated with 1.6M butyl lithium in hexane (31.25 ml, 50 mM). The resulting anion solution was heated to reflux then treated with a solution of diisopropylcyanamide (6.3 g, 50 mM) in benzene (15 ml). After 15 min. the mixture was cooled and quenched with water (20 ml). The organic phase was separated, dried and evaporated. Distillation of the residue gave the title compound (5.6 g, 71%) Bp. 135°-140°/2 mm, identical with authentic material. Hydrochloride mp 185° C.--see Example 37 UK Pat. No. 1,432,378.

Workup

  1. temperatureThe resulting anion solution was heated
  2. temperatureto reflux
  3. temperatureAfter 15 min. the mixture was cooled
  4. customquenched with water (20 ml)
  5. customThe organic phase was separated
  6. customdried
  7. customevaporated
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-ccb67ea9f9f643a2a75c71a84c978a19
Source dataset
uspto-grants-1985_07
Patent number
US04529798

Reaction notes

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