HCID 54468070, compound → HCID 53935000, compound

HRID 1763666Notes

Reaction equation

HRID 1763666 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[N:11]([CH:12]=1)[CH2:10][CH2:9][C:8]1[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=1[C:6]2=[CH:17][CH2:18][CH2:19][N:20](C)[C:21](OCC(Cl)(Cl)Cl)=O)#[N:2]>[Zn].C(O)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]2[N:11]([CH:12]=1)[CH2:10][CH2:9][C:8]1[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=1[C:6]2=[CH:17][CH2:18][CH2:19][NH:20][CH3:21])#[N:2]

Participants

4

Reactant 1

HCID 54468070HCID 54468070, compound

Product 1

HCID 53935000HCID 53935000, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2-Cyano-6,11-dihydro-11-(N-2,2,2-trichloroethoxycarbonyl-3-methylaminopropylidene)-5H-pyrrolo[2,1-b][3]benzazepine (4.0 g., 8.7 mmole) and zinc dust (8 g.) in 25 ml. acetic acid was stirred at room temperature for 18 hours. The solid was filtered off and washed with acetic acid. The filtrate was taken to dryness. The residue was dissolved in dilute hydrochloric acid and extracted with ethyl acetate. The aqueous phase was then made basic, extracted with methylene chloride; the organic layer was washed with water, dried over sodium sulfate and concentrated to yield 2-cyano-6,11-dihydro-11-(methylaminopropylidene)-5H-pyrrolo[2,1-b][3]benzazepine (2.3 g., 95%) as a brown oil.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with acetic acid
  3. dissolutionThe residue was dissolved in dilute hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. extractionextracted with methylene chloride
  6. washthe organic layer was washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5c868c703bc54b75960239814d7ba722
Source dataset
uspto-grants-1978_09
Patent number
US04112112

Reaction notes

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