6,7-dihydro-2H-benzo[6,7]cyclohepta[1,2-c]pyridazin-3(5H)-one → 5-Chloro-3,4-diazatricyclo(9.4.0.0,2,7)pentadeca-1(15),2(7),3,5,11,13-hexaene

HRID 1919470Notes

Reaction equation

HRID 1919470 reaction equation
O=[C:2]1[NH:7][N:6]=[C:5]2[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[CH2:10][CH2:11][CH2:12][C:4]2=[CH:3]1.O(Cl)[Cl:18].[P+3]>>[Cl:18][C:2]1[N:7]=[N:6][C:5]2[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[CH2:10][CH2:11][CH2:12][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 141261586,7-dihydro-2H-benzo[6,7]cyclohepta[1,2-c]pyridazin-3(5H)-oneHCID 178479710HCID 178479710, compound

Product 1

HCID 141261595-Chloro-3,4-diazatricyclo(9.4.0.0,2,7)pentadeca-1(15),2(7),3,5,11,13-hexaene

Procedure

Alternatively, 3-Oxo-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-c]pyridazine was heated with 20 mL of phosphorus (III) oxychloride at 100° C. for 4.75 h. The solvent was removed under vacuum. The residue was treated with ice and saturated sodium bicarbonate solution. The solid which formed was filtered off, washed well with water and air-dried to yield the corresponding 3-chloro-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-c]pyridazine (1.6 g); 1H NMR (CDCl3, 300 MHz) 7.82 (m, 1H), 7.44 (m, 2H), 7.39 (s, 1H), 7.27 (m, 1H), 2.55 (m, 4H), 2.32 (m, 2H) ppm; MS (ES) 231/233 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. additionThe residue was treated with ice and saturated sodium bicarbonate solution
  3. customThe solid which formed
  4. filtrationwas filtered off
  5. washwashed well with water
  6. customair-dried

Sources & evidence

ORD record
ord-3c85e8cce88043a79786efbbf4df3660
Source dataset
uspto-grants-2012_05
Patent number
US08168636B2

Reaction notes

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