Hydrochloric Acid → HCID 12803118, compound

HRID 652444Notes

Reaction equation

HRID 652444 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24].[C:25](OC(=O)C)(=[O:27])[CH3:26].O.Cl>N1C=CC=CC=1.C(OCC)(=O)C>[O:23]=[C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:24])[N:14]1[CH2:13][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([CH2:2][NH:1][C:25](=[O:27])[CH3:26])[CH:4]=2)[NH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 12803116HCID 12803116, compound

Product 1

HCID 12803118HCID 12803118, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

An ice-cold suspension of 2-[2-[5-(aminomethyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione, hemisulphate, hydrate (1.01 g) in pyridine (40 ml) was treated dropwise with acetic anhydride (0.6 ml). The mixture was stirred at room temperature for 1 h, water (15 ml) was added, and after a further 15 min the solution was acidified with hydrochloric acid (2N) and extracted into ethyl acetate (3×150 ml). The combined extract was washed with sodium carbonate (2N; 300 ml), dried (MgSO4) and evaporated to dryness, affording a yellow foam. On trituration with ethyl acetate (ca. 10 ml) this afforded the title amide as a pale yellow crystalline solid (0.79 g) m.p. 180°-2°.

Workup

  1. extractionextracted into ethyl acetate (3×150 ml)
  2. extractionThe combined extract
  3. washwas washed with sodium carbonate (2N; 300 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customaffording a yellow foam

Sources & evidence

ORD record
ord-14086d33178f418dbb510191ec435e6a
Source dataset
uspto-grants-1987_06
Patent number
US04672067

Reaction notes

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