HCID 380861, compound → HCID 380595, compound

HRID 976036Notes

Reaction equation

HRID 976036 reaction equation
C[O:2][C:3]1[C:12]([O:13]C)=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:15]([OH:17])=[O:16])=[CH:8]2>N1C=CC=CC=1>[C:4]1([CH2:5][CH2:6][O:17][C:15]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:12]([OH:13])[C:3]=3[OH:2])[CH:8]=2)=[O:16])[CH:9]=[CH:10][CH:11]=[CH:12][CH:3]=1

Participants

3

Reactant 1

HCID 380861HCID 380861, compound

Product 1

HCID 380595HCID 380595, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A total of 240 mg (1.0 mmol) of 5,6-dimethoxy-2-naphthoic acid (Burke, T. R., et al., J. Med. Chem. (1993) 36, 425-432) was heated neat with pyridine.HCL (5.0 g) at 180°-200° C. under argon (40 minutes). Excess pyridine.HCL was distilled off under high vacuum and residue mixed with 1N HCL (20 mL), giving 5,6-dihydroxy-2-naphtohoic acid a light yellow solid which was collected by filtration (160 mg). A 140 mg (0.7 mmol) portion was reacted β-phenylethyl alcohol as described for compound 67H-46-A and purified by silica gel chromatography (CHC3) to provide product 67H-52-A as a white solid (1200 mg, 36% yield overall): mp 164°-166° C.; 1HNMR (DMSO-d6) δ8.40 (d, 1H, J=1.6 Hz), 8.07 (d, 1H, J=8.8 Hz), 7.80 (dd, 1H, J=1.6 Hz & 8.8 Hz), 7.49 (d, 1H, J=8.6 Hz), 7.38-7.33 (m, 5H), 7.25 (d, 1H, J=8.6 Hz), 4.51 (t, 2H, J=6.8 Hz), 3.08 (t, 2H, J=6.8 Hz); FABMS (NBA,-VE)mz 307 (M--H). Anal. (C19H16O4) C,H.

Workup

  1. customat 180°-200° C.
  2. customunder argon (40 minutes)
  3. distillationHCL was distilled off under high vacuum and residue
  4. additionmixed with 1N HCL (20 mL)
  5. customgiving 5,6-dihydroxy-2-naphtohoic acid a light yellow solid which
  6. filtrationwas collected by filtration (160 mg)
  7. customA 140 mg (0.7 mmol) portion was reacted β-phenylethyl alcohol
  8. custompurified by silica gel chromatography (CHC3)
  9. customto provide product 67H-52-A as a white solid (1200 mg, 36% yield overall)

Sources & evidence

ORD record
ord-fb3805a7badc4f62b5ee3d43b40bf3e6
Source dataset
uspto-grants-1997_03
Patent number
US05610185

Reaction notes

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