Benzaldehyde → HCID 13535457, compound

HRID 1719613Notes

Reaction equation

HRID 1719613 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[C:12]([OH:21])[CH:13]=[CH:14][C:15]=3[OH:20])[C:10](=[O:22])[C:9]=2[C:8]([NH:23][CH2:24][CH2:25][NH2:26])=[CH:7][CH:6]=1.[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH:34](=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[OH:21][C:12]1[C:11]2[C:10](=[O:22])[C:9]3[C:18](=[C:5]([NH:4][CH2:3][CH2:2][N:1]=[CH:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:6]=[CH:7][C:8]=3[NH:23][CH2:24][CH2:25][N:26]=[CH:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:17](=[O:19])[C:16]=2[C:15]([OH:20])=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 1140TolueneHCID 125982CL 232468

Product 1

HCID 13535457HCID 13535457, compound

Procedure

A suspension of 2.00 g (0.0057 mole) of the free base, 1,4-bis[(2-aminoethyl)amino]-5,8-dihydroxyanthraquinone (prepared as described in Example 1) in 60 ml of toluene containing 1.82 g (0.0171 mole) of benzaldehyde was stirred and heated under reflux for 4 hours, using a Dean-Stark trap to remove by-product water. The hot reaction mixture was filtered to remove some residual solid which was washed with a minimal amount of toluene. The combined filtrate and wash was allowed to stand at room temperature for 13 days. The solid formed was collected by filtration and washed with a minimum of ether to yield 1.80 g of the product of the Example as a dark blue solid, mp 174°-179° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customto remove by-product water
  4. filtrationThe hot reaction mixture was filtered
  5. customto remove some residual solid which
  6. washwas washed with a minimal amount of toluene
  7. washThe combined filtrate and wash
  8. customThe solid formed
  9. filtrationwas collected by filtration
  10. washwashed with a minimum of ether

Sources & evidence

ORD record
ord-c24639330c2c4a6f8e59cd57b8ee3c4a
Source dataset
uspto-grants-1985_09
Patent number
US04540788

Reaction notes

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