Hydrochloric Acid → Ethyl-1-hydroxy-1,2,3,4-tetrahydronaphthalene-1-carboximidate

HRID 903151Notes

Reaction equation

HRID 903151 reaction equation
[C:1]([C:3]1([OH:13])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)#[N:2].Cl.[CH2:15]([OH:17])[CH3:16]>>[CH2:15]([O:17][C:1]([C:3]1([OH:13])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)=[NH:2])[CH3:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 157503811-Cyano-1-hydroxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 13053008Ethyl-1-hydroxy-1,2,3,4-tetrahydronaphthalene-1-carboximidate

Procedure

The cyanohydrin of Example 4 (6.0 g, 34.7 mmol) was dissolved in 60 ml ethanol and perfused with hydrogen chloride for 30 minutes. After a 16 hour reaction period at 0° C. the mixture was evaporated in vacuo to a solid which was triturated with ether. The residue was taken up in 200 ml chloroform and washed with 2×50 ml saturated sodium bicarbonate, 1×50 ml brine, dried over sodium sulfate, filtered, and concentrated to a solid; 5.3 g (71%), mp 84°-86° C.

Workup

  1. customAfter a 16 hour reaction period at 0° C. the mixture
  2. customwas evaporated in vacuo to a solid which
  3. customwas triturated with ether
  4. washwashed with 2×50 ml saturated sodium bicarbonate, 1×50 ml brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-44d53ec7784b4f6eaf07330e6bf7f557
Source dataset
uspto-grants-1980_10
Patent number
US04226875

Reaction notes

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