Aluminium lithium hydride → HCID 55273148, compound

HRID 520219Notes

Reaction equation

HRID 520219 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([CH3:13])[CH:7]=1)[C:3](O)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([CH3:13])[CH:7]=1)[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 552715891239646-77-5

Product 1

HCID 55273148HCID 55273148, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-amino-2-(4-chloro-3-methylphenyl)acetic acid (1.7 g, 8.5 mmol) in tetrahydrofuran (0.4 M) at 0° C. was added lithium aluminum hydride (2 M, 8.5 mL, 17 mmol) dropwise. The reaction was refluxed for 18 hours. The reaction was cooled and quenched with ice water. The reaction was extracted with ethyl acetate, washed with water, and brine. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to provide the title compound as a yellow solid (1.6 g, quantitative): 1H NMR (300 MHz, DMSO-d6) δ 7.44-7.23 (m, 2H), 7.18 (dd, J=8.2, 2.2 Hz, 1H), 4.77 (bs, 2H), 3.81 (dd, J=7.8, 4.8 Hz, 1H), 3.53-3.14 (m, 3H), 2.30 (s, 3H); ESIMS m/z 186 ([M+H]+).

Workup

  1. temperatureThe reaction was refluxed for 18 hours
  2. temperatureThe reaction was cooled
  3. customquenched with ice water
  4. extractionThe reaction was extracted with ethyl acetate
  5. washwashed with water, and brine
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0ced9e0d69674281b0a56358ce6b2bc9
Source dataset
uspto-grants-2016_05
Patent number
US09326516B2

Reaction notes

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