Isopropanol → HCID 16730397, compound

HRID 507332Notes

Reaction equation

HRID 507332 reaction equation
O1[C:3]2[CH:4]=[CH:5][C:6]3[C:7]4[C:12]([NH:13][C:14]=3[C:2]1=2)=[CH:11][CH:10]=[CH:9][CH:8]=4.[CH3:15][O:16][C:17]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20].C([O:30][CH2:31][CH3:32])(=O)C.C[CH:34]([OH:36])C>>[CH:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[C:5]([O:36][CH2:34][CH:31]([OH:30])[CH2:32][NH:20][CH2:19][C:18]2[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:17]=2[O:16][CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 3776Isopropanol2×HCID 8857Ethyl AcetateHCID 5972502,4-DimethoxybenzylamineHCID 22461213HCID 22461213, compound

Product 1

HCID 16730397HCID 16730397, compound

Procedure

To a stirred solution of Epoxy carbazole (5 gm, 0.0209 mole) in IPA (20 ml), 2,4-dimethoxybenzylamine (9.42 ml, 0.06276 moles) was added, and the reaction mixture was heated to reflux for 3 hours. Subsequently the reaction mixture was cooled and IPA was stripped off. To the semisolid residue obtained, ethyl acetate (50 ml) was added and it was refluxed for 1.5 hours, until everything dissolved. A light yellow colored clear solution was finally obtained, which was stirred at room temperature for 5 hours when it completely crystallized out as a white solid (8 g, 94.2%), m.p: 152-154° C., 1H NMR (400 MHz, CDCl3): δ 2.89(m 1H), 2.99(d 1H), 3.74(s 3H), 3.78(s 3H), 3.81(d 2H), 4.27(m, 3H), 6.42(m 2H), 6.65(d 1H), 7.08(d 1H), 7.14(m 2H), 7.29(m 1H), 7.35(d 1H), 7.43(d 1H), 8.22(d 1H), 9.42(s 1H); m/zM+1 406.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperatureSubsequently the reaction mixture was cooled
  4. customTo the semisolid residue obtained
  5. temperatureit was refluxed for 1.5 hours, until everything
  6. dissolutiondissolved
  7. customA light yellow colored clear solution was finally obtained
  8. customcompletely crystallized out as a white solid (8 g, 94.2%), m.p: 152-154° C., 1H NMR (400 MHz, CDCl3): δ 2.89(m 1H), 2.99(d 1H), 3.74(s 3H), 3.78(s 3H), 3.81(d 2H), 4.27(m, 3H), 6.42(m 2H), 6.65(d 1H), 7.08(d 1H), 7.14(m 2H), 7.29(m 1H), 7.35(d 1H), 7.43(d 1H), 8.22(d 1H), 9.42(s 1H)

Sources & evidence

ORD record
ord-c0359c9a2cf847e28d003bd50f86cfe5
Source dataset
uspto-grants-2010_08
Patent number
US07786142B2

Reaction notes

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