Toluene → HCID 23333707, compound

HRID 904266Notes

Reaction equation

HRID 904266 reaction equation
O=[C:2]1[CH2:11][CH:10]2[N:5]([CH2:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=32)[CH2:4][CH2:3]1.[CH3:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1)=[O:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O.CN(C)C=O>[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][CH:2]2[CH2:11][CH:10]3[N:5]([CH2:6][CH2:7][C:8]4[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=43)[CH2:4][CH2:3]2)=[CH:22][CH:21]=1)(=[O:18])[CH3:16]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 312304-AminoacetanilideHCID 111483532H-Benzo[a]quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-

Product 1

HCID 23333707HCID 23333707, compoundYield 14.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,3,4,6,7,11b-hexahydro-2-oxo-2H-benzo[a]quinolizine (8 g, 0.04 mole; prepared as described by Beke et al), 4-aminoacetanilide (6 g, 0.04 mole), a catalytic amount of p-toluenesulfonic acid (TsOH), 150 ml of toluene and 25 ml of dimethylformamide (DMF) was refluxed for 18 hours with the water produced being collected in a Dean-Stark trap. The solvent was removed in vacuo and the concentrate dissolved in 150 ml of methanol and cooled in an ice bath whereupon 8 g of NaBH4 was added in portions. At this point the mixture was stirred in the cold for 1 hour and at about 18° C. overnight. The solvent was removed in vacuo, the concentrate crystallized from acetone and petroleum ether and recrystallized from benzene and petroleum ether to yield 2 g of the desired product, m.p. 210°-3°.

Workup

  1. customproduced
  2. custombeing collected in a Dean-Stark trap
  3. customThe solvent was removed in vacuo
  4. dissolutionthe concentrate dissolved in 150 ml of methanol
  5. temperaturecooled in an ice bath whereupon 8 g of NaBH4
  6. additionwas added in portions
  7. customat about 18° C.
  8. customovernight
  9. customThe solvent was removed in vacuo
  10. customthe concentrate crystallized from acetone and petroleum ether
  11. customrecrystallized from benzene and petroleum ether

Sources & evidence

ORD record
ord-9d96b6736b6b4a05b5bf440819504bca
Source dataset
uspto-grants-1980_10
Patent number
US04230710

Reaction notes

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