2-Amino-6-chlorobenzoic acid → HCID 67740431, compound

HRID 375615Notes

Reaction equation

HRID 375615 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8]([OH:10])=O.ClC1C(OC)=C(Cl)C(OC)=C2C=1C[N:16]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][C:17]1=N2>C1(C)C=CC=CC=1>[Cl:1][CH:2]1[CH2:3][CH2:4][CH2:5][C:6]2[N:11]=[C:32]3[CH2:31][CH:30]=[CH:29][CH:28]=[CH:17][N:16]3[C:8](=[O:10])[C:7]1=2

Participants

4

Reactant 2

HCID 750712-Amino-6-chlorobenzoic acidHCID 18992783HCID 18992783, compound2×

Product 1

HCID 67740431HCID 67740431, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

18.01 g 6-chloroanthranilic acid suspended in 100 mL toluene was treated with 14 mL 1-aza-2-methoxy-1-cycloheptene (1) and refluxed with stirring under a Dean-Stark trap to remove the forming water and methanol for 1 hour. An exothermic reaction ensued, forming a two-layer mixture and foaming considerably. This gradually dissolved, giving a brown solution. Then 9 mL of (1) was added and the mixture was refluxed for 18 more hours. The toluene was removed in vacuo and excess of (1) was distilled out at 11 mmHg at 140° C. bath. The residue was chromatographed (6:1 chloroform-ethyl acetate) and recrystallized from hexane-ethyl acetate. The product, 1-chloro-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one, was obtained as a white, crystalline solid, m.p. 128° C.-129° C.; yield 16.5 g.

Workup

  1. temperaturerefluxed
  2. customto remove the forming water and methanol for 1 hour
  3. customAn exothermic reaction
  4. customforming a two-layer mixture
  5. dissolutionThis gradually dissolved
  6. customgiving a brown solution
  7. temperaturethe mixture was refluxed for 18 more hours
  8. customThe toluene was removed in vacuo and excess of (1)
  9. distillationwas distilled out at 11 mmHg at 140° C. bath
  10. customThe residue was chromatographed (6:1 chloroform-ethyl acetate)
  11. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-cea0a9b5b4d543e1973fd9e5c928ddd0
Source dataset
uspto-grants-1996_01
Patent number
US05486512

Reaction notes

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