Triethylamine → 9-[3'-(Isopropylaminocarbonyloxymethyl)-anilino]-2,7-dimethoxyacridine

HRID 484087Notes

Reaction equation

HRID 484087 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[CH:19]=[C:18]([O:21][CH3:22])[CH:17]=[CH:16]3)=[CH:12][CH:11]=[C:10]([O:23][CH3:24])[CH:9]=2.[CH:28]([N:31]=[C:32]=[O:33])([CH3:30])[CH3:29].C(N(CC)CC)C>C(Cl)Cl>[CH:28]([NH:31][C:32]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[CH:19]=[C:18]([O:21][CH3:22])[CH:17]=[CH:16]3)=[CH:12][CH:11]=[C:10]([O:23][CH3:24])[CH:9]=2)=[O:33])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 19749149HCID 19749149, compound

Product 1

HCID 197494999-[3'-(Isopropylaminocarbonyloxymethyl)-anilino]-2,7-dimethoxyacridineYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 9-(3'-hydroxymethylanilino)-2,7-dimethoxyacridine, (300 mg, 0.66 mmol), isopropyl isocyanate (1 ml) and triethylamine (2 ml) in methylene chloride (20 ml) is stirred at room temperature for 90 minutes, and then concentrated in vacuo. The residue is chromatographed on a silica gel column using commerical chloroform as the eluent to give the 9-[3'-(isopropylaminocarbonyloxymethyl)-anilino]-2,7-dimethoxyacridine, (246 mg, 84%) as a yellow solid, mp 148°-149° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is chromatographed on a silica gel column

Sources & evidence

ORD record
ord-2c6c5ec64e9f43f29d6b28bb62d13f9f
Source dataset
uspto-grants-1993_07
Patent number
US05229395

Reaction notes

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