Phthalic Anhydride → HCID 59767867, compound

HRID 1170834Notes

Reaction equation

HRID 1170834 reaction equation
Cl.[CH3:2][O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][NH:8][NH:7]1)=[O:5].[C:12]1(=O)[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[CH3:2][O:3][C:4]([C@H:6]1[N:7]2[C:12](=[O:17])[C:13]3[C:14]([C:15](=[O:16])[N:8]2[CH2:9][CH2:10][CH2:11]1)=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:5]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 81531DiisopropylethylamineHCID 66846189HCID 66846189, compound

Product 1

HCID 59767867HCID 59767867, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (S)-hexahydro-pyridazine-3-carboxylic acid methyl ester hydrochloride (Y. Nakamura, C. J Shin, Chem. Lett, 1991, 11, 1953-1956) (370 mg, 2.05 mmol), phthalic anhydride (318 mg, 2.15 mmol) and diisopropylethylamine (291 mg, 2.25 mmol) was heated in toluene (5 mL) for 2 h. The reaction mixture was then cooled and partitioned between ethyl acetate and dilute HCl. The organic phase was washed with saturated aq. NaHCO3, dried (MgSO4), filtered and evaporated. The residue was crystallised from hexane and filtered to afford the title compound as a white solid (562 mg, 82%): 1H NMR (400 MHz, CD3OD) δ 1.59 (1H, m), 1.96 (1H, m), 2.17 (1H, m), 2.55 (1H, m), 3.38 (1H, m), 3.70 (3H, s), 4.89 (1H, m), 5.74 (1H, m), 7.89 (2H, m), 8.16 (2H, m). 13C NMR (100 MHz, CD3OD) δ 21.2 (CH2), 25.7 (CH2), 46.0 (CH2), 53.8 (CH), 58.1 (CH3), 129.0 (CH), 129.1 (CH), 130.1 (C), 130.6 (C), 135.3 (CH), 135.7 (CH), 160.4 (C), 162.4 (C), 171.7 (C).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. custompartitioned between ethyl acetate and dilute HCl
  3. washThe organic phase was washed with saturated aq. NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallised from hexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-bbbeb34e4bed46679e0c039fd64567ad
Source dataset
uspto-grants-2010_11
Patent number
US07829561B2

Reaction notes

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