Water → HCID 847921, compound

HRID 1190888Notes

Reaction equation

HRID 1190888 reaction equation
C[Al](C)C.[NH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.[NH2:10][C:11]1[CH:12]=[C:13]([C:21]([O:23]C)=O)[CH:14]=[C:15]([C:17]([O:19]C)=O)[CH:16]=1.O>C(Cl)Cl>[N:5]1([C:21]([C:13]2[CH:12]=[C:11]([CH:16]=[C:15]([C:17]([N:5]3[CH2:9][CH2:8][CH2:7][CH2:6]3)=[O:19])[CH:14]=2)[NH2:10])=[O:23])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 66831Dimethyl 5-aminoisophthalateHCID 16682925Trimethylaluminum

Product 1

HCID 847921HCID 847921, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of AlMe3 (2M in toluene, 19.5 mL, 2 eq) was added dropwise to a solution of pyrrolidine (3.25 mL, 2 eq) in 50 mL of anhydrous DCM at 0° C. The reaction mixture was allowed to warm up to room temperature and stirred for 1 h. 1,3-Dimethyl 5-aminobenzene-1,3-dicarboxylate (4.10 g, 19.5 mmol) was added and the reaction mixture was refluxed for 38 h. The mixture was then poured in ice cooled water and filtered. The aqueous filtrate was extracted with CHCl3. The combined organic layers were dried over MgSO4, filtered and evaporated to give 3.5 g of expected compound which was used in the next step without further purification.

Workup

  1. temperaturethe reaction mixture was refluxed for 38 h
  2. additionThe mixture was then poured in ice
  3. filtrationfiltered
  4. extractionThe aqueous filtrate was extracted with CHCl3
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-191966e0bdb84e6fafee2f8480bd80c6
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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