Hydrochloric Acid → HCID 178518628, compound

HRID 977190Notes

Reaction equation

HRID 977190 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:19][CH2:20][C:21]#[N:22])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+].Cl.C(N(CC)CC)C.Cl>CN1CCCC1=O.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:19][CH2:20][C:21]3[NH:25][N:24]=[N:23][N:22]=3)=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 10781154HCID 10781154, compound

Product 1

HCID 178518628HCID 178518628, compoundYield 9.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 7-chloro-4-(2-cyanoethyl)-3-phenyl-quinolin-2(1H)-one (Example 39, 0.45 g) in 1-methyl-2-pyrrolidinone (50 ml) under nitrogen at room temperature, was added sodium azide (0.28 g) followed by triethylamine hydrochloride (0.30 g). The reaction mixture was heated to 150° C. and stirred for 48 h. After allowing to cool, the mixture was poured into water (100 ml), acidified to pH 1 with concentrated HCl and extracted with ethyl acetate (3×75 ml). The combined organic layers were extracted with 1N sodium hydroxide (3×75 ml) and the combined aqueous phases were washed with diethyl ether (2×75 ml), then acidified to pH 1 using concentrated HCl. The aqueous layer was extracted with ethyl acetate (3×75 ml) and the combined organic layers were dried (MgSO4), filtered and the solvent was removed in vacuo to leave a solid residue. Recrystallisation from a water/methanol mix then from ethyl acetate gave the title compound (0.05 g). Mp 231°-233° C. Found: C, 61.31; H, 4.20; N, 19.41; C18H14N5OCl. 0.1 H2O requires C, 61.14; H, 4.05; N, 19.81%. δ (360 MHz, DMSO-d6) δ 3.05 (4H, bs, CH2CH2Tet)), 7.10-7.42 (7H, m, Ph+6-H+8-H), 7.86 (1H, d, J=8.73 Hz, 5-H), 12.00 (1H, bs, NH). m/z (CI+), 352, (M+1).

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (3×75 ml)
  3. extractionThe combined organic layers were extracted with 1N sodium hydroxide (3×75 ml)
  4. washthe combined aqueous phases were washed with diethyl ether (2×75 ml)
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×75 ml)
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customto leave a solid residue
  10. customRecrystallisation from a water/methanol
  11. additionmix

Sources & evidence

ORD record
ord-a65db01d909f45fd9d56e0a822a4e2a3
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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