Formic Acid → HCID 178420717, compound

HRID 1858368Notes

Reaction equation

HRID 1858368 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[C:18]=2[NH2:24])=[CH:2]1.[CH:25](O)=O>>[N:23]1[C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([O:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11][CH2:10][C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)[C:18]=2[NH:24][CH:25]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 112442363-{2-[3-(1H-Indol-3-yl)-propylamino]-ethoxy}-benzene-1,2-diamine

Product 1

HCID 178420717HCID 178420717, compound

Conditions

Temperature
104 °C

Procedure

A solution of 3-{2-[3-(1H-indol-3-yl)-propylamino]-ethoxy}-benzene-1,2-diamine (0.75 g, 2.3 mmol) dissolved in 15 ml formic acid (98%) was heated to 104° C. for 6 hours. Upon standing overnight at 25° C., the excess formic acid was removed by vacuum distillaton. Water (100 ml) and ethyl acetate (100 ml) was added thereto. The ethyl acetate layer was separated and washed once with water (50 ml), once with brine (75 ml) and dried over anhydrous magnesium sulfate. Concentration of the solvent gave 0.7 g of product as a brown solid. Purification by chromatography (2 N ammonia in methanol:methylene chloride=20:1.5) and crystallization from ethyl acetate-ethanol afforded 0.345 g (44.8%) of product as a white solid: mp 121-124° C. decomposed. The HCl salt was prepared in ethanol: mp 256-258° C. decomposed.

Workup

  1. customthe excess formic acid was removed by vacuum distillaton
  2. additionWater (100 ml) and ethyl acetate (100 ml) was added
  3. customThe ethyl acetate layer was separated
  4. washwashed once with water (50 ml), once with brine (75 ml)
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-1f94b07d75614d6c9c6578ef02ada0d8
Source dataset
uspto-grants-2000_11
Patent number
US06150533

Reaction notes

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