Hydrochloric Acid → 2-Oxo-1,2,3,4-tetrahydroquinoxaline-6-carbonitrile
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
Product 1
Reagents, catalysts & solvents 2
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
- customThe solid was collected
- washwashed with Et2O
- customdried by air
Sources & evidence
- ORD record
- ord-5bf7cd393fed401ca62f42c4d5097d8c
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06207697B1
Reaction notes
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