Hydrochloric Acid → HCID 57471403, compound

HRID 2177106Notes

Reaction equation

HRID 2177106 reaction equation
[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[N:19])[CH:16]=2)[CH2:11][CH2:10][CH:9]1[NH:20]C(=O)OC(C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>ClCCl.C(O)(C)C>[NH2:20][CH:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:17]2[CH:16]=[C:15]([C:18]#[N:19])[CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57467306HCID 57467306, compound

Product 1

HCID 57471403HCID 57471403, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 1-benzyl-7-cyano-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (1.1 g, 3.03 mmol) was dissolved in dichloromethane (20 mL) and 5 M hydrochloric acid in isopropanol (2 mL) was added. The reaction mixture was stirred at room temperature for 12 h followed by 4 h at 35° C. The solvent was evaporated in vacuo. Water (30 mL) was added and the pH was adjusted to pH 9 using aqueous saturated sodium bicarbonate solution. The aqueous layer was extracted with dichloromethane. The combined extracts were dried (MgSO4) and the solvent was evaporated in vacuo. Yield: 790 mg (3.03 mmol, 100%).

Workup

  1. waitfollowed by 4 h at 35° C
  2. customThe solvent was evaporated in vacuo
  3. additionWater (30 mL) was added
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-8c42ed1b23834162ab2ee3def9a7b610
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Reaction notes

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