HCID 131711954, compound → HCID 131711952, compound

HRID 225022Notes

Reaction equation

HRID 225022 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][NH:23]CC2C=CC(O)=C(OC)C=2)[CH:6]=[CH:5][C:4]=1[OH:34].C(N[CH:39]1[C:48]2[C:47]([C:49]([O:51][CH3:52])=[O:50])=[N:46][N:45]=[C:44]([C:53]([O:55][CH3:56])=[O:54])[C:43]=2[CH2:42][CH2:41][CH2:40]1)(=O)C>[Zn].C(O)(=O)C>[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:34].[C:3]([NH:45][N:46]1[C:44]([C:53]([O:55][CH3:56])=[O:54])=[C:43]2[CH2:42][CH2:41][CH2:40][CH2:39][C:48]2=[C:47]1[C:49]([O:51][CH3:52])=[O:50])(=[O:2])[CH3:4]

Participants

4

Reactant 1

HCID 131711954HCID 131711954, compound

Product 1

HCID 131711952HCID 131711952, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

A solution was prepared by adding 2.59 g. of dl-6-acetamido-1,4-di(carbomethoxy)-5,6,7,8-tetrahydrobenzo[d]pyridazine to 100 ml. of glacial acetic acid. 5 g. of zinc dust were added and the resulting mixture stirred at ambient temperature for about 1 day. An additional 5 g. of zinc dust were added after 6 hours. The reaction mixture was then filtered to remove unreacted zinc dust and the resulting filtrate poured over ice. The filtrate was made basic with 14 N aqueous ammonium hydroxide and the alkaline mixture extracted several times with a chloroform-isopropanol solvent combination. The organic extracts were separated and combined, and the combined extracts washed with saturated aqueous sodium chloride and then dried. Evaporation of the solvent therefrom yielded dl-5-acetamido-1,3-di(carbomethoxy)-4,5,6,7-tetrahydro-2H-benzo[c]pyrrole formed in the above reaction; yield=1.83 g. Recrystallization from methanol yielded crystalline material melting at 231°-232° C.

Workup

  1. customA solution was prepared
  2. additionby adding 2.59 g
  3. filtrationThe reaction mixture was then filtered
  4. customto remove unreacted zinc dust
  5. additionthe resulting filtrate poured over ice
  6. extractionthe alkaline mixture extracted several times with a chloroform-isopropanol solvent combination
  7. customThe organic extracts were separated
  8. washthe combined extracts washed with saturated aqueous sodium chloride
  9. customdried
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-eb715aec3fc04bd7a5e6aaf34f63f76d
Source dataset
uspto-grants-1980_11
Patent number
US04235776

Reaction notes

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