L-Proline → HCID 68699150, compound

HRID 1157670Notes

Reaction equation

HRID 1157670 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14]([OH:16])=[O:15]>CN1CCOCC1>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:12]2[CH2:19][CH2:18][CH2:17][C@H:13]2[C:14]([OH:16])=[O:15])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 145742L-ProlineHCID 445509712-Chloro-4-fluoro-3-methylbenzonitrile

Product 1

HCID 68699150HCID 68699150, compound

Reagents, catalysts & solvents 1

HCID 79724-MethylmorpholineSolvent

Procedure

Heat a slurry of 2-chloro-4-fluoro-3-methyl-benzonitrile (0.4 g, 2.36 mmol) and L-proline (2.11 g, 18.8 mmol) in N-methylmorpholine (1.6 mL) at 200° C. in a microwave for 30 min. Partition the reaction between 2N aqueous hydrochloric acid and ethyl acetate. Separate and extract the organic portion with 2N aqueous sodium hydroxide. Acidify the aqueous extract to pH 1 by adding concentrated hydrochloric acid and back extract into ethyl acetate. Extract the combined organic portions with brine, dry over magnesium sulphate, filter, and concentrate under reduced pressure to give the title compound. (0.395 g, 63%) mass spectrum (m/e): 263 (M−1); 1H NMR (300 MHz, CDCl3): δ 8.66 (bs, 1H0, 7.31 (d, 1H), 6.75 (d, 1H), 4.38 (t, 1H), 3.67 (m, 1H), 3.10 (m, 1H), 2.43 (m, 1H), 2.29 (s, 3H), 2.20-1.90 (m. 3H).

Workup

  1. customPartition
  2. customthe reaction between 2N aqueous hydrochloric acid and ethyl acetate
  3. customSeparate
  4. extractionextract the organic portion with 2N aqueous sodium hydroxide
  5. extractionaqueous extract to pH 1
  6. additionby adding concentrated hydrochloric acid
  7. extractionback extract into ethyl acetate
  8. extractionExtract the combined organic portions with brine
  9. dry with materialdry over magnesium sulphate
  10. filtrationfilter
  11. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-f5dd8f2d87e64493ab2e677390f6e893
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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