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

HRID 1400095Notes

Reaction equation

HRID 1400095 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-6d7ff7af32d7463c9fd09201078c0757
Source dataset
uspto-grants-2014_12
Patent number
US08906922B2

Reaction notes

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