Water → {3-Chloro-8-[(dimethylamino)methyl]naphthalen-2-yl}methanol

HRID 1968754Notes

Reaction equation

HRID 1968754 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[C:25]([Cl:26])=[CH:24][C:23]2[C:18](=[C:19]([CH2:27][N:28]([CH3:30])[CH3:29])[CH:20]=[CH:21][CH:22]=2)[CH:17]=1)=O)C.O>C1COCC1>[Cl:26][C:25]1[C:16]([CH2:14][OH:13])=[CH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:27][N:28]([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 668827963-Chloro-8-dimethylaminomethyl-naphthalene-2-carboxylic acid ethyl ester

Product 1

HCID 66882407{3-Chloro-8-[(dimethylamino)methyl]naphthalen-2-yl}methanolYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutylaluminium hydride (1M in THF, 4.2 ml, 4.1 mmol, 9.0 equiv) was added to a solution of 3-chloro-8-dimethylaminomethyl-naphthalene-2-carboxylic acid ethyl ester (133 mg, 0.46 mmol) in 3.2 ml anhydrous THF at 0° C. After 15 minutes at 0° C., TLC analysis revealed complete conversion of starting material. Water (30 ml) was added, and the mixture was extracted with EtOAc (2×100 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (gradient of CH2Cl2/MeOH 97:3 to 90:10) afforded the title compound (109 mg, 96%, mixture of 2 regioisomers) as a colorless oil. Data for (3-chloro-8-dimethylaminomethyl-naphthalen-2-yl-methanol: 1H NMR (400 MHz, CDCl3): δ=8.36 (s, 1H), 7.85 (s, 1H), 7.74 (dd, J=7.1/1.9 Hz, 1H), 7.44-7.39 (m, 2H), 4.94 (s, 2H), 4.06 (s, 2H), 2.45 (s, 6H). MS (ES+): 250 (M+H)+.

Workup

  1. extractionthe mixture was extracted with EtOAc (2×100 ml)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via flash chromatography (gradient of CH2Cl2/MeOH 97:3 to 90:10)

Sources & evidence

ORD record
ord-b0b2b98f074e4edc902befd4b8eb48b0
Source dataset
uspto-grants-2013_04
Patent number
US08426440B2

Reaction notes

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