HCID 10346280, compound → HCID 9979116, compound

HRID 1707741Notes

Reaction equation

HRID 1707741 reaction equation
[CH2:1]([CH2:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][O:16]C(=O)CCC(C)=O)[CH:12]=[C:11]([NH:24][C:25]2[C:26]3[C:31]([N:32]=[C:33]4[C:38]=2[CH:37]=[CH:36][CH:35]=[CH:34]4)=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:10]=1)=[O:7])[C:2]([CH3:4])=[O:3].C[O-].[Na+]>N1C=CC=CC=1>[CH2:1]([CH2:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[C:11]([NH:24][C:25]2[C:26]3[C:31]([N:32]=[C:33]4[C:38]=2[CH:37]=[CH:36][CH:35]=[CH:34]4)=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:10]=1)=[O:7])[C:2]([CH3:4])=[O:3]

Participants

4

Reactant 2

HCID 10346280HCID 10346280, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 9979116HCID 9979116, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of N,O-bis(acetonylacetyl)-3-(9-acridinylamino)-5-hydroxymethylaniline (423 mg, 0.83 mmol) in methanolic sodium methoxide [prepared from sodium (15 mg, 0.65mmol) in MeOH (15 mL)] is stirred at room temperature for 2 days. The mixture is passed through an ion-exchange resin (Dowex 50 in pyridine form). The product is eluted with a mixture of pyridine/H2O (v/v 1:1). The combined eluate is evaporated in vacuo to dryness. The product is purified by chromatography (SiO2, CHCl3 /MeOH, v/v 15:1) to give N-acetonylacety-3-(9-acridinylamino)-5-hydroxymethylaniline, 217 mg (64.0%), mp 197°-199° C. 1H-NMR (DMSO-d6): δ 2.10 (3H, s, COCH3), 4.35 (2H, broad singlet, CH2 --OH), 6.42 (1H, broad singlet, ArH), 6.90 (1H, broad singlet, ArH), 6.89-7.18 (2H, m, ArH), 7.19 (1H, broad singlet, ArH), 7.50-7.76 (4H, m, ArH), 8.30-8.48 (2H, m, ArH, 9.76 (1H, s, NH). Analyses: Calculated for C25H23N3O3 : C, 72.62; H, 5.61; N, 10.16. Found: C, 72.53; H, 5.46; N, 9.99.

Workup

  1. washThe product is eluted with a mixture of pyridine/H2O (v/v 1:1)
  2. customThe combined eluate is evaporated in vacuo to dryness
  3. customThe product is purified by chromatography (SiO2, CHCl3 /MeOH, v/v 15:1)

Sources & evidence

ORD record
ord-4111da4e8dec4fa5885ca55d05e8b2d4
Source dataset
uspto-grants-1994_10
Patent number
US05354864

Reaction notes

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