Dimethyl acetylenedicarboxylate → HCID 68917540, compound

HRID 1958524Notes

Reaction equation

HRID 1958524 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[F:23])[C:5]([N:7]1[CH:16](C(O)=O)[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)=O.[C:24]([C:30]([O:32][CH3:33])=[O:31])#[C:25][C:26]([O:28][CH3:29])=[O:27]>C(OC(=O)C)(=O)C>[CH3:29][O:28][C:26]([C:25]1[C:24]([C:30]([O:32][CH3:33])=[O:31])=[C:5]([C:4]2[CH:20]=[CH:21][C:22]([F:23])=[C:2]([F:1])[CH:3]=2)[N:7]2[C:16]=1[CH2:15][C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:8]2)=[O:27]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 68915141HCID 68915141, compound

Product 1

HCID 68917540HCID 68917540, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-(3,4-difluorobenzoyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (11.10 g, 35 mmol) and dimethyl acetylenedicarboxylate (7.39 g, 52 mmol) in acetic anhydride (70 mL) was heated at 60-70° C. for 15 min. The reaction mixture was then cooled and evaporated in vacuo to dryness. The solid residue was recrystallized from ethanol to give 3-(3,4-difluorophenyl)-5,10-dihydropyrrolo[1,2-b]isoquinoline-1,2-dicarboxylic acid dimethyl ester 10.97 g, (78.6%); mp 142-144° C.; 1H NMR (DMSO-d6) δ 3.61 (3H, s, Me), 3.77 (3H, s, Me), 4.31 (2H, s, CH2), 5.00 (2H, s, CH2), 7.21-7.27 (1H, m, ArH), 7.29-7.35 (3H, m, 3×ArH), 7.37-7.43 (1H, m, ArH), 7.50-7.65 (2H, m, 2×ArH); m/z 397.00 (M+H)+ Anal. Calcld. for C22H17F2NO4: C, 66.50; H, 4.31; N, 3.52. Found: C, 66.65; H, 4.51; N, 3.47.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customevaporated in vacuo to dryness
  3. customThe solid residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-814744a8d4cb41dc9b3f7497a3899976
Source dataset
uspto-grants-2013_04
Patent number
US08410130B2

Reaction notes

Loading…