2-Methylbenzylamine → HCID 67520987, compound

HRID 1926243Notes

Reaction equation

HRID 1926243 reaction equation
[CH3:1][O:2][CH:3]([O:8][CH3:9])[C:4](OC)=[O:5].[CH3:10][C:11]1[C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=[CH:13][CH:12]=1>CCOC(C)=O>[CH3:1][O:2][CH:3]([O:8][CH3:9])[C:4]([NH:18][CH2:17][C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:10])=[O:5]

Participants

4

Reactant 2

HCID 69932-MethylbenzylamineHCID 66647Acetic acid, 2,2-dimethoxy-, methyl ester

Product 1

HCID 67520987HCID 67520987, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of methyl dimethoxyacetate (2.11 g, 15.6 mmol) and o-xylylamine (1.90 g, 15.4 mmol) in a 15 mL sealed tube was stirred at 55° C. for 11 d. The reaction solution was dissolved in EtOAc (≈60 mL) and washed with dil. HCl, water, sat. NaHCO3 solution, and brine, and dried over MgSO4. The EtOAc extract was filtered, concentrated, and dried in vacuo overnight to give the title compound as pale yellow oil. 1H NMR (400 MHz, CDCl3): δ=7.25-7.16 (m, 4H), 6.69 (brs, 1H), 4.75 (s, 1H), 4.48 (d, J=5.6 Hz, 2H), 3.40 (s, 6H), 2.33 (s, 3H). MS(ES+): m/z=246.07 (83) [MNa+], 224.11 (100) [MH+], 192.14 (60) [MH+-MeOH], 160.10 (95) [MH+-2 MeOH]. HPLC: tR=2.82 min (polar—5 min, ZQ3).

Workup

  1. customsealed tube
  2. washwashed with dil. HCl, water, sat. NaHCO3 solution, and brine
  3. dry with materialdried over MgSO4
  4. extractionThe EtOAc extract
  5. filtrationwas filtered
  6. concentrationconcentrated
  7. customdried in vacuo overnight

Sources & evidence

ORD record
ord-e6b4b93a46f54576b8e0ddbc7a5c1905
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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