HCID 178479710, compound → 2-Chloro-5,6-dihydrobenzo[h]quinazoline

HRID 531176Notes

Reaction equation

HRID 531176 reaction equation
[N:1]1[C:2](=O)[NH:3][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:2]1[N:3]=[CH:4][C:5]2[CH2:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[C:10]=2[N:1]=1

Participants

3

Reactant 2

HCID 178479710HCID 178479710, compoundHCID 178517332HCID 178517332, compound

Product 1

HCID 534860272-Chloro-5,6-dihydrobenzo[h]quinazoline

Procedure

5,6-Dihydrobenzo[h]quinazolin-2(3H)-one (2.97 g) was heated at 100° C. in phosphorus (III) oxychloride (70 mL) for 2 h. The solvent was removed under vacuum and the residue was treated with ice, followed by 1M aqueous potassium carbonate solution. The aqueous solution was extracted with a mixture of ether and ethyl acetate, dried over anhydrous sodium sulfate and concentrated under vacuum to give 2-chloro-5,6-dihydrobenzo[h]quinazoline as a yellow solid; 1H NMR (CDCl3/MeOD4, 300 MHz) 8.86 (s, 1H), 8.16 (m, 1H), 7.25-7.35 (m, 2H), 7.15 (m, 1H), 2.85 (m, 4H) ppm; 13C NMR (CDCl3/MeOD4, 75 MHz) 162.83, 159.45, 157.40, 139.60, 132.35, 130.99, 128.38, 127.61, 127.20, 126.14, 27.39, 24.11; MS (ES) 217/219 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. additionthe residue was treated with ice
  3. extractionThe aqueous solution was extracted with a mixture of ether and ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8a2b5d949bc24717a18a4b2524ea8e16
Source dataset
uspto-grants-2016_05
Patent number
US09353126B2

Reaction notes

Loading…