Triethylamine → HCID 69516786, compound

HRID 854939Notes

Reaction equation

HRID 854939 reaction equation
[NH2:1][C:2]1[C:9]([Br:10])=[CH:8][C:7]([Br:11])=[CH:6][C:3]=1[CH:4]=O.C(N(CC)CC)C.[F:19][C:20]([F:29])([F:28])/[CH:21]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(OCC)(=O)C>CS(C)=O>[Br:11][C:7]1[CH:6]=[C:3]2[C:2](=[C:9]([Br:10])[CH:8]=1)[NH:1][CH:21]([C:20]([F:19])([F:29])[F:28])[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:4]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 6883052-Amino-3,5-dibromobenzaldehydeHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoate

Product 1

HCID 69516786HCID 69516786, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The 2-amino-3,5-dibromobenzaldehyde (6.50 g, 23.3 mmol), triethylamine (6.96 g, 69.9 mmol) and ethyl 4,4,4-trifluorocrotonate (7.85 g, 46.6 mmol) were mixed in dimethylsulfoxide (12.0 mL) at 90° C. for 48 h. The solution was cooled to room temperature and the solution poured into ethyl acetate (100 mL). The solution was extracted with saturated aqueous ammonium chloride (2×100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The ethyl 6,8-dibromo-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylate (4.3 g, 10.0 mmol) was isolated as a yellow solid by flash silica chromatography (43% yield): MS m/z 428 (M−H, calcd 428).

Workup

  1. extractionThe solution was extracted with saturated aqueous ammonium chloride (2×100 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-852307a6c9ee40f9bca5df414ead329c
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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