Acetic Acid → HCID 86748624, compound

HRID 381611Notes

Reaction equation

HRID 381611 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:16]2[C:25]3[CH2:24][CH2:23][C:22](=[O:26])[CH2:21][C:20]=3[CH:19]=[CH:18][CH:17]=2)[C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].C([C:31]([O:33][CH3:34])=[O:32])#N.C(O)(=O)C>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[CH2:24][CH2:23][C:22]([OH:26])=[C:21]3[C:31]([O:33][CH3:34])=[O:32])[C:10](=[O:15])[C:11]([F:13])([F:12])[F:14])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 28660Carbonocyanidic acid, methyl esterHCID 23507839HCID 23507839, compound

Product 1

HCID 86748624HCID 86748624, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-(4-cyanophenyl)-2,2,2-trifluoro-N-(5,6,7,8-tetrahydro-6-oxo-1-naphthyl)acetamide (1.17 g, 3.27 mmol) in THF (15 ml) was added dropwise over a 15 minute period to a stirred suspension of 80% NaH (0.30 g, 10 mmol) (Aldrich) in methyl cyanoformate (1.5 ml, 19 mmol) (Aldrich) and THF (15 ml) under nitrogen. The reaction mixture was stirred 30 minutes at room temperature then quenched with acetic acid (0.7 ml, 12 mmol). The solution was concentrated in vacuo onto silica gel (3 g) and the absorbed material purified by chromatography on silica gel (30 g) eluting with ether:hexane (1:4 to 1:3) to give methyl 5-(N-(4-cyanophenyl)-2,2,2-trifluoroacetamido)-3,4-dihydro-2-hydroxy-1-naphthalene carboxylate (0.64 g). 1H NMR (CDCl3, 200 MHz) δ: 2.5-2.9 (m, 4H, CH2CH2), 3.93 (s, 3H, CH3), 7.10 (d, J=8 Hz, 1H, Ar), 7.32 (t, J=8 Hz, 1H, Ar), 7.39 (d, J=9 Hz, 2H, Ar), 7.64 (d, J=9 Hz, 2H, Ar), 7.82 (d, J=8 Hz, 1H, Ar), 13.35 (s, 1H, OH). Anal. Calculated for C21H15F3N2O4: C, 60.58; H, 3.63; N, 6.73. Found: C, 60.66; H, 3.66; N, 6.68.

Workup

  1. concentrationThe solution was concentrated in vacuo onto silica gel (3 g)
  2. customthe absorbed material purified by chromatography on silica gel (30 g)
  3. washeluting with ether:hexane (1:4 to 1:3)

Sources & evidence

ORD record
ord-f470d11c054447c4bd2790c0af0ee4a6
Source dataset
uspto-grants-2001_10
Patent number
US06306865B1

Reaction notes

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