Acetic Anhydride → 1-Methyl-1,2,3,4-tetrahydroquinoline-6-carbonitrile

HRID 1481678Notes

Reaction equation

HRID 1481678 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]=[N:13]O)=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.CC(OC(C)=O)=O>>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 78919842HCID 78919842, compound

Product 1

HCID 620964851-Methyl-1,2,3,4-tetrahydroquinoline-6-carbonitrileYield 63%

Conditions

Temperature
110 °C

Procedure

1-Methyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde oxime (8.0 g, ca. 42.0 mmol) and Ac2O (40 mL, 423.9 mmol, 10.1 eq) was mixed at room temperature then the mixture was heated to 110° C. and stirred for 4 h. The solvent was removed under reduced pressure then the residue was placed on ice (500 g). The resulting mixture was quenched with saturated aqueous NaHCO3 then extracted by CH2Cl2 (4×50 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was purified by flash column chromatography (0-25% EtOAc in hexanes) to afford the title compound (4.53 g, 26.3 mmol, 63% over two steps).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe resulting mixture was quenched with saturated aqueous NaHCO3
  3. extractionthen extracted by CH2Cl2 (4×50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationthen concentrated
  6. customto give a crude product which
  7. customwas purified by flash column chromatography (0-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6c430cc8d31c4a03a41bdda84994f0e4
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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