Benzo(h)cinnolin-3(2H)-one, 5,6-dihydro- → 3-Chloro-5,6-dihydrobenzo[h]cinnoline

HRID 531178Notes

Reaction equation

HRID 531178 reaction equation
[N:1]1[NH:2][C:3](=O)[CH:4]=[C:5]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[CH2:7][CH2:6]2.O(Cl)[Cl:17].[P+3]>>[Cl:17][C:3]1[N:2]=[N:1][C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 213230Benzo(h)cinnolin-3(2H)-one, 5,6-dihydro-HCID 178479710HCID 178479710, compound

Product 1

HCID 104433233-Chloro-5,6-dihydrobenzo[h]cinnoline

Procedure

5,6-Dihydrobenzo[h]cinnolin-3(2H)-one (4.5 g) was heated at 100° C. with phosphorus (III) Oxychloride (80 mL) for 6.5 h. The solvent was removed under vacuum and the residue was treated with ice water. The resulting solid was filtered off, washed well with water and air dried to give 3-chloro-5,6-dihydrobenzo[h]cinnoline; 1H NMR (DMSO-d6, 300 MHz) 8.32 (m, 1H), 7.36 (s, 1H), 7.32 (m, 2H), 7.19 (d, 1H), 2.91 (s, 4H) ppm; MS (ES) 217/219 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. additionthe residue was treated with ice water
  3. filtrationThe resulting solid was filtered off
  4. washwashed well with water and air
  5. customdried

Sources & evidence

ORD record
ord-f36f20f6d5c540a580b7fca848fb1641
Source dataset
uspto-grants-2016_05
Patent number
US09353126B2

Reaction notes

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