Isopropylamine → 3-Hydroxy-N-(1-methylethyl)benzamide

HRID 412050Notes

Reaction equation

HRID 412050 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.CN1CCOCC1.[CH:18]([NH2:21])([CH3:20])[CH3:19].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH:18]([NH:21][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([OH:1])[CH:3]=1)([CH3:20])[CH3:19]

Participants

7

Reactant 5

HCID 6363IsopropylamineHCID 74203-Hydroxybenzoic AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 283905573-Hydroxy-N-(1-methylethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Hydroxybenzoic acid (0.966 g, 7.0 mmol), N-methylmorpholine (2.3 mL, 21 mmol), iso-propylamine (1.78 mL, 21 mmol) and CH2Cl2 (30 mL) were dissolved together and hydroxybenzotriazole (1.03 g, 7.7 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.47 g, 7.7 mmol) was added; stirred 16 h, diluted with CH2Cl2 (70 mL) and the organic phase was washed with satd aq NaHCO3, H2O, 0.3 N HCl, H2O, and satd aq NaCl, dried (Na2SO4) and concentrated to afford 443 mg as a white foam. 1H NMR (CDCl3): d 7.23 (m, 3), 6.90 (m, 1), 4.22 (m, 1), 1.25 (d, 6).

Workup

  1. washthe organic phase was washed with satd aq NaHCO3, H2O, 0.3 N HCl, H2O
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto afford 443 mg as a white foam

Sources & evidence

ORD record
ord-ba39b23b0b4a4065b6c9684c6e6836ae
Source dataset
uspto-grants-2003_05
Patent number
US06562832B1

Reaction notes

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