Carbon Dioxide → HCID 68919869, compound

HRID 1958507Notes

Reaction equation

HRID 1958507 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10](O)=O.[C:13]([C:19](OC)=O)#[C:14][C:15]([O:17][CH3:18])=[O:16].C(=O)=O.[C:26]([O:29][C:30](=O)C)(=[O:28])C>>[CH3:30][O:29][C:26]([C:10]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[N:1]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[CH2:3][C:2]=12)=[O:28]

Participants

5

Reactant 4

HCID 280Carbon Dioxide2×HCID 7918Acetic AnhydrideHCID 12980Dimethyl acetylenedicarboxylateHCID 86074Indoline-2-carboxylic acid

Product 1

HCID 68919869HCID 68919869, compound

Procedure

A mixture of indoline 2-carboxylic acid (10.60 g, 65 mmol) and dimethyl acetylenedicarboxylate (9.24 g, 80 mmol) in acetic anhydride (110 mL) was stirred in a flask equipped with a reflux condenser and a gas bubbler to monitor carbon dioxide evolution during the reaction. The mixture was heated to 120° C. where carbon dioxide evolution was most intense. The temperature was maintained until gas evolution had ceased (ca. 10 h). The dark solution was concentrated in vacuo and the solid residue was crystallized from methanol to yield 3-methyl-8H-3a-aza-cyclopenta[a]indene-1,2-dicarboxylic acid dimethyl ester, 14.40 g (78%): mp 162-164° C.; 1H NMR (DMSO-d6) δ 2.74 (3H, s, Me), 3.85 and 3.89 (each 3H, s, 2×OMe), 4.01 (2H, s, CH2) 7.20-7.27 (1H, m, ArH), 7.33-7.37 (1H, m, ArH), 7.46-7.53 (2H, m, 2×ArH). Anal. Calcd. for C16H15NO4: C, 67.36; H, 5.30; N, 4.91. Found: C, 67.30; H, 5.31; N, 4.85.

Workup

  1. customequipped with a reflux condenser
  2. customduring the reaction
  3. temperatureThe temperature was maintained until gas evolution
  4. custom(ca. 10 h)
  5. concentrationThe dark solution was concentrated in vacuo
  6. customthe solid residue was crystallized from methanol

Sources & evidence

ORD record
ord-753e069d76784be6b0e404cbbf119593
Source dataset
uspto-grants-2013_04
Patent number
US08410130B2

Reaction notes

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