Methanol → HCID 71544871, compound

HRID 1403707Notes

Reaction equation

HRID 1403707 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:15]3[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[CH:19][C:20]=3[C:21](=[O:22])[C:13]=2[C:12]2[C:7](=[CH:8][C:9]([N+:25]([O-])=O)=[CH:10][CH:11]=2)[C:6]1=[O:28].CO.C(OCC)(=O)C>O1CCCC1>[NH2:25][C:9]1[CH:8]=[C:7]2[C:12]([C:13]3[C:21](=[O:22])[C:20]4[CH:19]=[C:18]([O:23][CH3:24])[CH:17]=[CH:16][C:15]=4[C:14]=3[N:5]([CH2:4][CH2:3][CH2:2][Br:1])[C:6]2=[O:28])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8857Ethyl AcetateHCID 71544870HCID 71544870, compound

Product 1

HCID 71544871HCID 71544871, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(3-Bromopropyl)-9-methoxy-3-nitro-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione (80, 1.00 g, 2.26 mmol) was dissolved in tetrahydrofuran (60 mL), methanol (20 mL), and ethyl acetate (30 mL) and transferred to a Parr shaker flask. The reaction vessel was purged with argon for 10 min and then palladium-charcoal (10%, 20 mg) was added. The reaction mixture was shaken for 24 h under an atmosphere of hydrogen (60 psi). The solid was filtered off, the solvent removed under vacuum, and the compound purified by silica gel column chromatography, eluting with ethyl acetate. The product was obtained as a brown solid (0.55 g, 59%): mp 330° C. (dec). IR (Film) 3367, 1696, 1655, 1506, 1480, 1431, 1293, 1229, 1016, 834, 787, 665 cm−1; 1H NMR (300 MHz, DMSO-d6) δ 8.35 (d, J=8.6 Hz, 1 H), 7.67-7.62 (m, 2 H), 7.06 (d, J=2.5 Hz, 1 H), 7.0.1-6.94 (m, 2 H), 4.51 (t, J=6.0 Hz, 2 H), 3.84 (s, 3 H), 3.75 (dd, J=7.5 Hz, J=6.6 Hz, 2 H), 2.30 (br p, J=8.5 Hz, 2 H); EIMS m/z (rel intensity) 413 (M+, 46), 333 ([M-HBr)]+, 100); HRESIMS m/z calcd for C20H17N2O3Br 413.0501 (MH+), found, 413.0505 (MH+).

Workup

  1. customThe reaction vessel was purged with argon for 10 min
  2. additionpalladium-charcoal (10%, 20 mg) was added
  3. filtrationThe solid was filtered off
  4. customthe solvent removed under vacuum
  5. customthe compound purified by silica gel column chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-b3ddb74961ee499cbaf4f75d3672b437
Source dataset
uspto-grants-2014_12
Patent number
US08912213B2

Reaction notes

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