Acetic Acid → HCID 61609705, compound

HRID 2244358Notes

Reaction equation

HRID 2244358 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(O[C:15]1(O[Si](C)(C)C)[CH2:17][CH2:16]1)C.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Cl:11][C:8]1[CH:9]=[CH:10][C:2]([NH:1][CH:15]2[CH2:17][CH2:16]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 124762-Amino-5-chlorobenzoic acidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 61609705HCID 61609705, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 500 mg of 2-amino-5-chloro-benzoic acid (2.91 mmol) in methanol were added 3 Å molecular sieves, 2.34 ml of [(1-ethoxycyclopropyl)oxy]trimethylsilane (11.66 mmol) and 1.67 ml of acetic acid and the mixture was stirred for 30 min at RT. Then 916 mg of sodium cyanoborohydride (14.57 mmol) were added and the reaction mixture was heated to reflux for 16 h. The reaction mixture was allowed to cool to RT, filtered and the filtrate was concentrated in vacuo. The remaining solid was dissolved in ethyl acetate and the solution was washed with 1N HCl and brine, dried (MgSO4), filtered and concentrated to give 312 mg of the crude title compound that was used in the following step without further purification. 1HNMR (DMSO-d6, 300 MHz): δ 0.46 (m, 2H), 0.79 (m, 2H), 3.44 (m, 1H), 7.10 (d, J=8.9 Hz, 1H), 7.44 (d, J=8.9 Hz, 1H), 7.70 (s, 1H), 7.89 (br s, 1H), 13.09 (br s, 1H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 16 h
  3. temperatureto cool to RT
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe remaining solid was dissolved in ethyl acetate
  7. washthe solution was washed with 1N HCl and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-94e0b28f68044d6c89874d0b7797d10a
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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