Hydrochloric Acid → HCID 15711995, compound

HRID 2292046Notes

Reaction equation

HRID 2292046 reaction equation
[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[CH2:5][C:4]([CH3:15])([CH3:14])[C@H:3]1[OH:16].C(N(CC)CC)C.Cl[CH2:25][CH2:26][CH2:27][C:28](Cl)=[O:29].Cl>ClCCl>[O:29]=[C:28]1[CH2:27][CH2:26][CH2:25][N:1]1[C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[CH2:5][C:4]([CH3:14])([CH3:15])[C@H:3]1[OH:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 15711991HCID 15711991, compound

Product 1

HCID 15711995HCID 15711995, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of trans-1-amino-3,3-dimethyl-7-cyano-1,2,3,4-tetrahydro-2-napthol (0.5 g), triethylamine (0.5 ml) and 4-chlorobutyrylchloride (0.33 g) in dichloromethane (35 ml) was stirred at room temperature for 1 h. The solution was poured into dilute hydrochloric acid, and the organic layer separated and washed with sodium carbonate solution and dried over magnesium sulphate. Removal of drying agent and solvent gave the crude amide (0.8 g), which was not purified further, but dissolved in dry tetrahydrofuran (60 ml) and sodium hydride (75 mg of 80% dispersion in oil) added portionwise, under nitrogen. The mixture was then stirred at room temperature for 1.5 h, then poured into water and extracted into ethyl acetate. The organic extracts were washed with brine and dried over magnesium sulphate. Removal of drying agent and solvent, followed by crystallisation of the residue from ethyl acetate: 60°-80° petrol (1:1) gave the title compound as colourless microcrystals (0.35 g) having m.p. 203°-4° C.

Workup

  1. customthe organic layer separated
  2. washwashed with sodium carbonate solution
  3. dry with materialdried over magnesium sulphate
  4. customRemoval
  5. customof drying agent and solvent
  6. customgave the crude amide (0.8 g), which
  7. customwas not purified further
  8. dissolutiondissolved in dry tetrahydrofuran (60 ml)
  9. additionsodium hydride (75 mg of 80% dispersion in oil) added portionwise, under nitrogen
  10. additionpoured into water
  11. extractionextracted into ethyl acetate
  12. washThe organic extracts were washed with brine
  13. dry with materialdried over magnesium sulphate
  14. customRemoval
  15. customof drying agent and solvent
  16. customfollowed by crystallisation of the residue from ethyl acetate

Sources & evidence

ORD record
ord-9a98df2af198445b9d59e34992f1bb15
Source dataset
uspto-grants-1989_01
Patent number
US04800212

Reaction notes

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