Hydrochloric Acid → HCID 10245999, compound

HRID 232028Notes

Reaction equation

HRID 232028 reaction equation
O.Cl.ICC([O:7][C:8]1[C:13]2[C:14](=[O:31])[C:15]3[C:27]([C:28](=[O:29])[C:12]=2[CH:11]=[CH:10][CH:9]=1)=[C:26]1[N:17]([CH2:18][C:19]2[C:24]([CH:25]1[CH3:30])=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=3)=O>O1CCCC1>[OH:7][C:8]1[C:13]2[C:14](=[O:31])[C:15]3[C:27]([C:28](=[O:29])[C:12]=2[CH:11]=[CH:10][CH:9]=1)=[C:26]1[N:17]([CH2:18][C:19]2[C:24]([CH:25]1[CH3:30])=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=3

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13691173HCID 13691173, compound2×

Product 1

HCID 10245999HCID 10245999, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Water (312 ml) and concentrated hydrochloric acid (169 ml) were added to a suspension of 5,8,13,14-tetrahydro-9-[iodoacetoxy]-14-methylbenz[5,6]isoindolo[2,1-b]isoquinolin-8,13-dione (80.0 g, Intermediate 9 in GB-A-2175587) in tetrahydrofuran (1.335 L). This mixture was stirred and heated to reflux under nitrogen for 18 h and part (550 ml) of the solvent was removed by distillation at atmospheric pressure. The resulting suspension was stirred and cooled to ca. 5° for 4.5 h, and the solid was collected by filtration, washed with cold tetrahydrofuran and dried in vacuo to give the title compound (48.8 g); λmax 243 nm (MeOH), E11 1022; δ(CDCl3) 12.98 (OH, s, 1H), 5.27 (5-H, d, 16 Hz, 1H), 5.16 (5-H, d, 16 Hz, 1H), 4.98 (14-H, q, 7 Hz, 1H), 1.55 (14-CH3, d, 7 Hz, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 18 h
  3. custompart (550 ml) of the solvent was removed by distillation at atmospheric pressure
  4. stirringThe resulting suspension was stirred
  5. temperaturecooled to ca. 5° for 4.5 h
  6. filtrationthe solid was collected by filtration
  7. washwashed with cold tetrahydrofuran
  8. customdried in vacuo

Sources & evidence

ORD record
ord-1318c5cb6e384c90b4c0790551a5b7fa
Source dataset
uspto-grants-1989_07
Patent number
US04851399

Reaction notes

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