Hydrochloric Acid → HCID 21980629, compound

HRID 11038Notes

Reaction equation

HRID 11038 reaction equation
Cl.[Si]([O:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[CH:24]=[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])[C:22]3[C:33](=[O:37])[NH:34][C:35](=[O:36])[C:21]=3[C:20]=2[C:19]2[CH:18]=[C:17]([O:38][CH3:39])[CH:16]=[CH:15][C:14]1=2)(C(C)(C)C)(C)C>C1COCC1.CO>[Cl:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:23]1[C:22]2[C:33](=[O:37])[NH:34][C:35](=[O:36])[C:21]=2[C:20]2[C:19]3[CH:18]=[C:17]([O:38][CH3:39])[CH:16]=[CH:15][C:14]=3[N:13]([CH2:12][CH2:11][CH2:10][OH:9])[C:25]=2[CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 695840016-(3-{[tert-Butyl(dimethyl) silyl]oxy}propyl)-4-(2-chlorophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 21980629HCID 21980629, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

3N HCl (50 mL) was added to a solution of 6-(3-{[tert-Butyl(dimethyl) silyl]oxy}propyl)-4-(2-chlorophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (4.87 g, 8.85 mmol) prepared according to example 39 in 1:1 THF/methanol (200 mL). After stirring at room temperature for 2 h most of the solvents were removed in vacuo, the residue was extracted with ethyl acetate, washed well with water and the organic portion was concentrated to a volume of 60 mL. Petroleum ether was added to precipitate the product, which was filtered off and triturated several times with diethyl ether. The solid was crystallised from THF/petroleum ether and gave 4-(2-Chlorophenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-chlorophenyl, R10═CH2CH2CH2OH) (31)in a 3.77 g, 88% yield as a yellow powder; mp 228–230° C. 1H NMR δ [(CD3)2SO] 11.12 (br s, 1H), 8.52 (d, J=2.5 Hz, 1H), 7.80 (s, 1H), 7.70 (d, J=8.9 Hz, 1H), 7.58 (dd, J=8.1, 22 Hz, 1H), 7.53–7.42 (m, 3H), 7.31 (dd, J=8.9, 2.5 Hz, 1H), 4.63 (br, 1H), 4.53 (t, J=6.9 Hz, 2H), 3.91 (s, 3H), 3.40 (m, 2H), 1.91 (m, 2H). Found: C, 66.00; H, 4.23; N, 6.55. C24H19ClN2O4 requires C, 66.29; H, 4.40; N, 6.44.

Workup

  1. customprepared
  2. customwere removed in vacuo
  3. extractionthe residue was extracted with ethyl acetate
  4. washwashed well with water
  5. concentrationthe organic portion was concentrated to a volume of 60 mL
  6. additionPetroleum ether was added
  7. customto precipitate the product, which
  8. filtrationwas filtered off
  9. customtriturated several times with diethyl ether
  10. customThe solid was crystallised from THF/petroleum ether

Sources & evidence

ORD record
ord-a94facf86c9243e5a21ad99eb2b723d6
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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