Dimethyl acetylenedicarboxylate → HCID 68919114, compound

HRID 1958513Notes

Reaction equation

HRID 1958513 reaction equation
[C:1]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]1C(O)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([C:27]([O:29][CH3:30])=[O:28])#[C:22][C:23]([O:25][CH3:26])=[O:24]>C(OC(=O)C)(=O)C>[CH3:26][O:25][C:23]([C:22]1[C:21]([C:27]([O:29][CH3:30])=[O:28])=[C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:9]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:11][C:10]=12)=[O:24]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 12842041HCID 12842041, compound

Product 1

HCID 68919114HCID 68919114, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-benzoyl-2,3-dihydro-1H-indole-2-carboxylic acid (7.48 g, 28 mmol) and dimethyl acetylenedicarboxylate (4.55 g, 32 mmol) in acetic anhydride (40 mL) was heated for 4.5 h at 120° C. until no gas was eliminated. The dark solution was concentrated in vacuo to dryness and the solid residue was recrystallized from methanol to yield 3-phenyl-8H-3a-azacyclopenta[a]indene-1,2-dicarboxylic acid dimethyl ester, 7.5 g (77%): mp 149-151° C.; 1H NMR (DMSO-d6) δ 3.62 (3H, s, OMe), 3.79 (3H, s, OMe), 4.15 (2H, s, CH2), 6.60-6.67 (1H, m, ArH), 7.18-7.23 (2H, m, 2×ArH), 7.51-7.67 (6H, m, 6×ArH). Anal. Calcd for C21H17NO4: C, 69.40; H, 5.21; N, 3.85. Found: C, 69.42; H, 4.65; N, 3.83.

Workup

  1. concentrationThe dark solution was concentrated in vacuo to dryness
  2. customthe solid residue was recrystallized from methanol

Sources & evidence

ORD record
ord-2a184ce949c24841a0dbe46734cb3167
Source dataset
uspto-grants-2013_04
Patent number
US08410130B2

Reaction notes

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