Hydrochloric Acid → HCID 86631948, compound

HRID 906139Notes

Reaction equation

HRID 906139 reaction equation
[CH2:1]([NH:3][C:4]1[C:5]([CH3:22])=[C:6]([CH:14]=[C:15]([CH3:21])[C:16]=1[C:17]([O:19]C)=[O:18])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH3:2].[OH-].[Li+].[OH-].[Na+].Cl>O1CCOCC1.O.CO>[C:10]([O:9][C:7]([C:6]1[CH:14]=[C:15]([CH3:21])[C:16]([C:17]([OH:19])=[O:18])=[C:4]([NH:3][CH2:1][CH3:2])[C:5]=1[CH3:22])=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 14798Sodium HydroxideHCID 86631947HCID 86631947, compound

Product 1

HCID 86631948HCID 86631948, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1-tert-Butyl 4-methyl 3-(ethylamino)-2,5-dimethylterephthalate (142 mg, 0.463 mmol) was dissolved in dioxane (2 mL) and was cooled in an ice bath. 2N Lithium hydroxide (0.25 mL) was added and the mixture was stirred for 16 h and then methanol (0.5 mL) and 2N lithium hydroxide (0.25 mL) were added, and the mixture was stirred at ambient temperature for 1.5 h. The mixture was cooled in an ice bath and 1N sodium hydroxide (0.5 mL) was added and the mixture was stirred for 1 h and then was warmed to ambient temperature and was stirred for a further 1 h. The mixture was stirred at 50-55° C. for a further 16 h and then was cooled to ambient temperature and acidified with 1N hydrochloric acid to pH ˜4.5. The mixture was diluted with water and extracted with ethyl acetate (2×). The organic portion was dried over sodium sulfate, then filtered and concentrated to provide 4-(tert-butoxycarbonyl)-2-(ethylamino)-3,6-dimethylbenzoic acid (115 mg, 0.392 mmol, 85% yield) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 7.45 (s, 1H), 2.97 (q, 2H), 2.67 (s, 3H), 2.46 (s, 3H), 1.61 (s, 9H), 1.34 (t, 3H); MS (EI) for C16H23NO4: 294 (MH+).

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringthe mixture was stirred at ambient temperature for 1.5 h
  3. temperatureThe mixture was cooled in an ice bath
  4. stirringthe mixture was stirred for 1 h
  5. stirringwas stirred for a further 1 h
  6. stirringThe mixture was stirred at 50-55° C. for a further 16 h
  7. temperaturewas cooled to ambient temperature
  8. extractionextracted with ethyl acetate (2×)
  9. dry with materialThe organic portion was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-0995a7f18a044132beab0f9b34176824
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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