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Sulfamic Acid → 3-Cyclopentyloxy-6-fluoro-4-methoxybenzoic acid

HRID 1092824
Notes
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Reaction equation

HRID 1092824 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:12]([F:17])=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)([OH:20])N.Cl([O-])=O.[Na+]>C(O)(=O)C.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:12]([F:17])=[CH:13][C:14]=2[O:15][CH3:16])[C:10]([OH:20])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 221457953-Cyclopentyloxy-6-fluoro-4-methoxybenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 221458483-Cyclopentyloxy-6-fluoro-4-methoxybenzoic acidYield 58.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent
HCID 962
Water
Solvent
2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-cyclopentyloxy-6-fluoro-4-methoxybenzaldehyde (1.4 g) in glacial acetic acid (20 mL) is treated with sulfamic acid (0.82 g) at room temperature and stirred for 10 minutes. The resulting yellow solution is cooled to 0° C. and treated with a solution of sodium chlorite (0.69 g of an 80% pure sample) in water (20 mL) during 10 minutes. The resulting yellow suspension is stirred at room temperature for 3 hours, poured into water (100 mL) and filtered to give 3-cyclopentyloxy-6-fluoro-4-methoxybenzoic acid (0.88 g), in the form of a white solid. [NMR (CDCl3): 7.46 (d, 1H, J=8 Hz), 6.65 (d, 1H, J=12 Hz), 4.80-0.76 (m, 1H), 3.90 (s, 3H), 2.01-1.58 (m, 8H)].

Workup

  1. stirringThe resulting yellow suspension is stirred at room temperature for 3 hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-5772c435a6634cf89eba82416b6d6bf5
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129537B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes