Water → HCID 23075071, compound

HRID 1785388Notes

Reaction equation

HRID 1785388 reaction equation
O[C:2]1[CH2:3][CH2:4][C:5](O)=[C:6]2[C:15]=1[C:14](=[O:16])[C:13]1[C:8](=[CH:9][C:10]([C:17]([OH:19])=[O:18])=[CH:11][CH:12]=1)[C:7]2=[O:20].[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1.O>C(O)CCCC.ClCCl.C1COCC1>[CH3:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8](=[CH:9][C:10]([C:17]([OH:19])=[O:18])=[CH:11][CH:12]=4)[C:7](=[O:20])[C:6]=3[C:5]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)=[CH:4][CH:3]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7813p-ToluidineHCID 178524096HCID 178524096, compound

Product 1

HCID 23075071HCID 23075071, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 62761-PentanolSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

1,4-Dihydroxy-2,3-dihydro-6-carboxy-anthraquinone (300 mg) Boric acid (300 mg) and p-Toluidine (1.8 g) is mixed in n-pentanol (5 mL) and heated to 110° C. for 4 hours, the mixture is co-evaporated with 2×50 ml of water. The residue is redissolved in dichloromethane/THF (1/1) 200 ml washed with water (3×100 mL) dried (Na2SO4), filtered and concentrated. The residue is purified on a silicagel column (CH2Cl2/MeOH/NEt3; 90/9/1) resulting in 350 mg of pure material. MALDI-MS: m/z 463.2 (M+H)

Workup

  1. washwashed with water (3×100 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified on a silicagel column (CH2Cl2/MeOH/NEt3; 90/9/1)

Sources & evidence

ORD record
ord-713cfdb2f0bd488dbe98e499c9e656bb
Source dataset
uspto-grants-2009_03
Patent number
US07504495B2

Reaction notes

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