Hydrochloric Acid → 4-[[(5,6,7,8-Tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)amino]carbonyl]benzoic acid methyl ester

HRID 265427Notes

Reaction equation

HRID 265427 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=O)=[CH:4][CH:3]=1.[CH3:14][C:15]1([CH3:27])[C:24]2[C:19](=[CH:20][C:21]([NH2:25])=[CH:22][CH:23]=2)[C:18](=[O:26])[CH2:17][CH2:16]1.Cl>S(Cl)(Cl)=O.CN(C)C=O>[CH3:14][C:15]1([CH3:27])[CH2:16][CH2:17][C:18](=[O:26])[C:19]2[CH:20]=[C:21]([NH:25][C:6]([C:5]3[CH:4]=[CH:3][C:2]([C:1]([O:12][CH3:13])=[O:11])=[CH:10][CH:9]=3)=[O:8])[CH:22]=[CH:23][C:24]1=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 36144541,4-Benzenedicarboxylic acid, methyl esterHCID 154628417-Amino-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 537129964-[[(5,6,7,8-Tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)amino]carbonyl]benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of monomethyl terephthalate (VIIIa) (2.86 g, 15.89 mmoles) in thionylchloride (50 mL) with 2 drops of N,N-dimethylformamide was allowed to stir at room temperature. The mixture became homogeneous within 30 minutes and was then concentrated in vacuo. The residue was then taken up in 30 mL of anhydrous pyridine and treated with 4,4-dimethyl-7-amino-1-tetralone (3.00 g, 15.9 mmoles). After 16 hours at room temperature 1N HCl was added to the mixture. It was extracted with ethyl acetate, washed with 1N HCl (4×200 mL) and washed with saturated sodium bicarbonate (2×200 mL). The organic phase was then separated, dried over magnesium sulfate, and concentrated in vacuo to give 5.07 g (Y: 91%) of the title compound; 1H-NMR (CDCl3): δ 8.27 (dd, J=8.7, 2.5 Hz, 1H), 8.19 (bs, 1H), 8.14 (d, J=8.4 Hz, 2H), 7.95 (d, J=8.4 Hz, 2H), 7.91 (d, J=2.5 Hz, 1H), 7.46 (d, J=8.7 Hz, 1H), 3.94 (s, 3H), 2.70 (t, J=7.0 Hz, 3H), 2.00 (t, J=7.0 Hz, 3H), 1.38 (s, 6H); MS (DCI) m/e: 352 (MH+).

Workup

  1. concentrationwas then concentrated in vacuo
  2. extractionIt was extracted with ethyl acetate
  3. washwashed with 1N HCl (4×200 mL)
  4. washwashed with saturated sodium bicarbonate (2×200 mL)
  5. customThe organic phase was then separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1cc84077bffd4189b493272dd357df63
Source dataset
uspto-grants-1997_07
Patent number
US05648385

Reaction notes

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