Water → HCID 21076641, compound

HRID 1374542Notes

Reaction equation

HRID 1374542 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11])(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:17]1[C:27]2=[C:28]3[C:23](=[CH:24][CH:25]=[CH:26]2)[CH2:22][CH2:21][CH2:20][N:19]3[C:18]1=[O:29].O>C(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([CH:21]1[CH2:22][C:23]2[C:28]3=[C:27]([CH2:17][C:18](=[O:29])[N:19]3[CH2:20]1)[CH:26]=[CH:25][CH:24]=2)=[O:11])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 13398872HCID 13398872, compoundHCID 149184935,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one

Product 1

HCID 21076641HCID 21076641, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
0 °C

Procedure

6-Acetyloxyhexanoic acid chloride (16.7 g, 86.6 mmol) in absolute CH2Cl2 (50 ml) is added in drops at 0° C. within 10 minutes to a suspension of anhydrous aluminum chloride (61.5 g, 461.6 mmol) in absolute CH2Cl2 (500 ml), and it is stirred for 15 minutes at this temperature. 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one (10.0 g (57.7 mmol) in absolute CH2Cl2 (100 ml) is added in drops within 15 minutes at 0° C., then it is heated to boiling temperature and stirred for 30 minutes. It is cooled to 0° C., hydrolyzed with ice and dispersed between water (300 ml) and CH2Cl2 (100 ml). The aqueous phase is extracted with CH2Cl2 (2×100 ml), the combined organic phases are washed with 2N hydrochloric acid (2×250 ml), water (2×250 ml), semi-concentrated aqueous Na2CO3 solution (2×250 ml), concentrated aqueous Na2CO3 solution (2×250 ml) and concentrated common salt solution (1×250 ml), dried (sodium sulfate/activated carbon), and the solvent is removed in a rotary evaporator.

Workup

  1. temperatureit is heated
  2. stirringstirred for 30 minutes
  3. extractionThe aqueous phase is extracted with CH2Cl2 (2×100 ml)
  4. washthe combined organic phases are washed with 2N hydrochloric acid (2×250 ml), water (2×250 ml), semi-concentrated aqueous Na2CO3 solution (2×250 ml), concentrated aqueous Na2CO3 solution (2×250 ml)
  5. concentrationconcentrated common salt solution (1×250 ml)
  6. dry with materialdried (sodium sulfate/activated carbon)
  7. customthe solvent is removed in a rotary evaporator

Sources & evidence

ORD record
ord-b7a9d7eee8904d508884fba524e09ee9
Source dataset
uspto-grants-2007_01
Patent number
US07166588B2

Reaction notes

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