Hydrochloric Acid → HCID 66750829, compound

HRID 643941Notes

Reaction equation

HRID 643941 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[C:10]([NH:23]C=O)[CH:9]=2)=[O:5])[CH3:2].Cl>CC(C)=O.O>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[C:10]([NH2:23])[CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86624021HCID 86624021, compound

Product 1

HCID 66750829HCID 66750829, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

5-Benzyloxy-6-formylamino-1H-indole-2-carboxylic acid ethyl ester (0.2 g, 0.591 mmol) is suspended in a 9:1 mixture of acetone/water (10 mL). The suspension is treated with 1N HCl (1.8 mL) and brought to reflux for 1 h. The separated solid is filtered, washed with saturated aqueous sodium bicarbonate and water, and air dried for 2 h to afford 6-amino-5-benzyloxy-1H-indole-2-carboxylic acid ethyl ester as a grey solid: (M−H)−=311.

Workup

  1. temperatureto reflux for 1 h
  2. filtrationThe separated solid is filtered
  3. washwashed with saturated aqueous sodium bicarbonate and water, and air
  4. customdried for 2 h

Sources & evidence

ORD record
ord-41f741bddac84de9bbf06e5e60ca4be4
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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