Hydrochloric Acid → 2-Oxo-1,2,3,4-tetrahydroquinoxaline-6-carbonitrile

HRID 1267154Notes

Reaction equation

HRID 1267154 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([C:14]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=1[NH2:22])C(OC(C)(C)C)=O)C.Cl.CCOCC>CO.O1CCOCC1>[C:20]([C:18]1[CH:19]=[C:14]2[C:15](=[CH:16][CH:17]=1)[NH:22][C:4](=[O:3])[CH2:5][NH:6]2)#[N:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 69839618HCID 69839618, compound

Product 1

HCID 185457712-Oxo-1,2,3,4-tetrahydroquinoxaline-6-carbonitrileYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

N-Boc-2-amino-5-cyanophenylglycin ethyl ester (2.6 g, 8.17 mmol) in MeOH (20 mL) was treated with 4M HCl in dioxane (20 mL) at rt for 16 hours. To the mixture was added Et2O until no more solid appeared. The solid was collected, washed with Et2O, and dried by air to give the product (1.4 g, 82%). 1H NMR (CD3COCD3) δ 7.02 (d, J=8.4 Hz, 1H), 7.00 (d, J=1.8 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 3.89 (s, 2H).

Workup

  1. customThe solid was collected
  2. washwashed with Et2O
  3. customdried by air

Sources & evidence

ORD record
ord-2ba1725105f24295a2b8f2e0e81d9bbd
Source dataset
uspto-grants-2003_04
Patent number
US06552042B2

Reaction notes

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