Reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]#N)=[CH:4][CH:3]=1.[OH-:14].[K+].[OH2:16]>>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:16])=[O:14])=[CH:4][CH:3]=1Participants
Procedure
4-Amino-1-naphthalenecarbonitrile (1.5 g, 8.91 mmol) was suspended in a 50% KOH solution (18 mL). The heterogeneous solution was heated at reflux for 2-3 days. Once the solution became homogeneous and TLC showed no more starting material, the deep red solution was cooled and poured over 200 mL of water. The resulting solution was then filtered and the desired product was precipitated with concentrated HCl. The resulting red crystals were filtered and the filtrate was refiltered to give pink crystals. The first fraction of crystals was treated with activated carbon to remove some of the red color. A total of 1.51 g of the desired product was obtained: m.p. 169-171° C.; 1H NMR (CD3OD) d 6.69 (1H, d, J=8.2 Hz), 7.38-7.43 (1H, m), 7.48-7.54 (1H, m), 8.03 (1H, d, J=8.5 Hz), 8.13 (1H, d, J=8.2 Hz), 9.09 (1H, d, J=8.5 Hz); 13C NMR (CD3OD) d 107.39, 114.61, 122.99, 123.92, 125.21, 127.40, 128.48, 135.04, 151.35, 171.44; HRMS Calc. for C11H7NO2, 187.0633; Found, 187.0642.
Workup
- temperatureThe heterogeneous solution was heated
- temperatureat reflux for 2-3 days
- temperaturethe deep red solution was cooled
- filtrationThe resulting solution was then filtered
- customthe desired product was precipitated with concentrated HCl
- filtrationThe resulting red crystals were filtered
- customto give pink crystals
- additionThe first fraction of crystals was treated with activated carbon
- customto remove some of the red color
Sources & evidence
- ORD record
- ord-c29061d91c3d4247aa1323a5bd40fa3d
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06204293B1
Linked notes
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