Sulfuric Acid → HCID 11701356, compound

HRID 1834476Notes

Reaction equation

HRID 1834476 reaction equation
[C:1]([CH2:3][CH:4]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:11][C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)#[N:2].S(=O)(=O)(O)O>[Pt]=O.C(O)(=O)C>[NH2:2][CH2:1][CH2:3][CH:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[O:11][C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 20373263HCID 20373263, compound

Product 1

HCID 11701356HCID 11701356, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

After the addition of 2 g. platinum oxide; 45 g. (0.21 mol) 9-cyanomethyl-xanthene in a mixture of 500 ml. glacial acetic acid and 5 ml. concentrated sulphuric acid are catalytically hydrogenated for 4 hours without the use of pressure. Subsequently, the acetic acid is substantially removed by evaporation in a vacuum (about 3/4 of the volume). The residue is taken up in water and the neutral products are removed by extraction with ether. The basic products are then liberated by the addition of 2N sodium hydroxide solution and isolated by extraction with ether. The evaporation residue of the ethereal solution gives, after high vacuum distillation, 28.4 g. (60% of theory) 9-(2-aminoethyl)-xanthene of b.p. 145° - 148° C./0.5 mm.Hg.

Workup

  1. additionAfter the addition of 2 g
  2. customSubsequently, the acetic acid is substantially removed by evaporation in a vacuum (about 3/4 of the volume)
  3. customthe neutral products are removed by extraction with ether
  4. additionThe basic products are then liberated by the addition of 2N sodium hydroxide solution
  5. customisolated by extraction with ether
  6. customThe evaporation residue of the ethereal solution gives
  7. distillationafter high vacuum distillation, 28.4 g

Sources & evidence

ORD record
ord-fa384bff92914000afd88fed41410a01
Source dataset
uspto-grants-1978_01
Patent number
US04070373

Reaction notes

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