Sodium Hydroxide → HCID 131711955, compound

HRID 225023Notes

Reaction equation

HRID 225023 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[C:25]([NH:28][N:29]1[C:33]([C:34]([O:36]C)=[O:35])=[C:32]2[CH2:38][CH2:39][CH2:40][CH2:41][C:31]2=[C:30]1[C:42]([O:44]C)=[O:43])(=[O:27])[CH3:26].[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[C:25]([NH:28][N:29]1[C:33]([C:34]([OH:36])=[O:35])=[C:32]2[CH2:38][CH2:39][CH2:40][CH2:41][C:31]2=[C:30]1[C:42]([OH:44])=[O:43])(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131711952HCID 131711952, compound

Product 1

HCID 131711955HCID 131711955, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A reaction mixture was prepared containing 1.8 g. of dl-5-acetamido-1,3-di(carbomethoxy)-4,5,6,7-tetrahydro-2H-benzo[c]pyrrole, 80 ml. of THF and 20 ml. of 2 N aqueous sodium hydroxide. The reaction mixture was heated to refluxing temperature under a nitrogen atmosphere for about 3 hours after which time it was cooled and the volatile constituents evaporated therefrom in vacuo. The residue was dissolved in 25 ml. of water and the aqueous solution made acidic by the addition of 1 N aqueous hydrochloric acid. The diacid, dl-5-acetamido-1,3-dicarboxy-4,5,6,7-tetrahydro-2H-benzo[c]pyrrole, formed in the above hydrolysis being insoluble in the acidic layer precipitated and was collected by filtration. Recrystallization from a benzene-methanol solvent mixture yielded crystalline diacid melting at 233°-235° C. with decomposition.

Workup

  1. customA reaction mixture was prepared
  2. additioncontaining 1.8 g
  3. temperatureThe reaction mixture was heated
  4. temperatureto refluxing temperature under a nitrogen atmosphere for about 3 hours after which time it
  5. temperaturewas cooled
  6. customthe volatile constituents evaporated
  7. dissolutionThe residue was dissolved in 25 ml
  8. additionof water and the aqueous solution made acidic by the addition of 1 N aqueous hydrochloric acid

Sources & evidence

ORD record
ord-e5e31a39316d4716a3c17e63cf735f58
Source dataset
uspto-grants-1980_11
Patent number
US04235776

Reaction notes

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