Acetic Acid → HCID 5127212, compound

HRID 2208832Notes

Reaction equation

HRID 2208832 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.O>[CH2:14]([NH:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 4313471Ethyl 3-Amino-2-methylbenzoateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 5127212HCID 5127212, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 3-amino-2-methylbenzoate (1.00 g, 5.58 mmol) in DCE (20 ml) was added benzaldehyde (569 μl, 5.58 mmol) followed by acetic acid (0.64 ml, 11.2 mmol). The reaction was stirred at room temperature for 1 h and then sodium triacetoxyborohydride (1.77 g, 8.37 mmol) was added and the reaction stirred for 2 h. Distilled water (20 ml) was added and solid NaHCO3 was added until the aqueous phase was pH7 and the phases were separated. The aqueous phase was washed with DCM (2×5 0 ml), the combined organics were then washed with brine (50 ml), dried using Na2SO4, filtered and evaporated to afford the title compound as a yellow oil (1.52 g, 96%) which was used in the next stage without any further purification. LC-MS 95%, m/z=270.0, 1H NMR (500 MHz, Chloroform-d) δ 7.42-7.32 (m, 4H), 7.32-7.28 (m, 1H), 7.17-7.06 (m, 2H), 6.73 (dd, J=7.8, 1.1 Hz, 1H), 4.40 (s, 2H), 4.36 (q, J=14.3, 5.3 Hz, 2H), 4.08 (br. s, 1H), 2.35, (s, 3H), 1.39 (t, 3H).

Workup

  1. stirringthe reaction stirred for 2 h
  2. customthe phases were separated
  3. washThe aqueous phase was washed with DCM (2×5 0 ml)
  4. washthe combined organics were then washed with brine (50 ml)
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-7267f3a5528f4070a239597283d86101
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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