5-Methoxysalicylic Acid → HCID 18765786, compound

HRID 1452772Notes

Reaction equation

HRID 1452772 reaction equation
Cl.[N+:2]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][CH:6]=1)([O-:4])=[O:3].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[CH3:36][O:37][C:38]1[CH:46]=[C:42]([C:43](O)=[O:44])[C:41]([OH:47])=[CH:40][CH:39]=1>ClCCl.O.C(N(CC)CC)C>[OH:47][C:41]1[CH:40]=[CH:39][C:38]([O:37][CH3:36])=[CH:46][C:42]=1[C:43]([NH:11][CH2:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:13][CH:12]=1)=[O:44]

Participants

8

Reactant 4

HCID 757875-Methoxysalicylic AcidHCID 458983Benzeneethanamine, 4-nitro-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 18765786HCID 18765786, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

4-nitrophenethylamine hydrochloride (1.81 g; 8.9 mmole), triethylamine (2.8 ml; 20=mole), hydroxybenzotriazole (1.45 g; 10.7 mmole) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (3.75 g; 19.62 mmole) are added to a solution of 1.5 g (8.9 mmole) of 5-methoxy-salicylic acid in dichloromethane (80 ml). The reaction medium is agitated overnight at 25° C. The mixture is diluted with 40 ml of water and agitated for ten minutes, then the product is extracted with dichloromethane. The organic solution is dried over sodium sulphate, filtered and concentrated under vacuum and the evaporation residue is purified on a silica column (eluent=ethyl acetate/heptane; 50/50) in order to produce a white solid which is obtained with a yield of 64%. Melting point: 200° C.

Workup

  1. stirringagitated for ten minutes
  2. extractionthe product is extracted with dichloromethane
  3. dry with materialThe organic solution is dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customthe evaporation residue is purified on a silica column (eluent=ethyl acetate/heptane; 50/50) in order
  7. customto produce a white solid which
  8. customis obtained with a yield of 64%

Sources & evidence

ORD record
ord-95de6fc9185c4f4ab19f0bd8cd15f747
Source dataset
uspto-grants-2009_01
Patent number
US07473779B2

Reaction notes

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