Hydrochloric Acid → HCID 69462263, compound

HRID 969450Notes

Reaction equation

HRID 969450 reaction equation
Cl[C:2](OC1C=CC=CC=1)=[O:3].[NH2:11][C:12]1[C:13]([OH:29])=[C:14]([C:26](=[O:28])[CH3:27])[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>N1C=CC=CC=1>[C:26]([C:14]1[C:13]2[O:29][C:2](=[O:3])[NH:11][C:12]=2[C:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15891Phenyl chloroformateHCID 579892521-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone

Product 1

HCID 69462263HCID 69462263, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
92.5 °C

Procedure

41 mL phenyl chloroformate are added dropwise to a solution of 47 g (183 mmol) 1-(3-amino-4-benzyloxy-2-hydroxy-phenyl)-ethanone (known from U.S. Pat. No. 4,460,581) in 135 mL pyridine, whereupon the temperature rises to 75° C. The mixture is stirred for 4 hours at 90-95° C., poured onto ice and acidified with hydrochloric acid. The precipitated solid is suction filtered, washed with diethyl ether and heated in 500 mL 95% acetonitrile for 30 minutes at reflux temperature. After cooling the solid is filtered off and washed with acetonitrile and diethyl ether.

Workup

  1. customrises to 75° C
  2. additionpoured onto ice
  3. filtrationfiltered
  4. washwashed with diethyl ether
  5. temperatureheated in 500 mL 95% acetonitrile for 30 minutes
  6. temperatureat reflux temperature
  7. temperatureAfter cooling the solid
  8. filtrationis filtered off
  9. washwashed with acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-5a694cac4c154f0a9f5479c0a7f8ca4c
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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