Triethylamine → 4-Hydroxy-3-nitrobenzoic acid

HRID 2273453Notes

Reaction equation

HRID 2273453 reaction equation
C1C=CC(C(Cl)(C2C(Cl)=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][C:27]=1[N+:35]([O-:37])=[O:36])(=O)C.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[OH:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][C:27]=1[N+:35]([O-:37])=[O:36]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 945242-Chlorotrityl chlorideHCID 140573074-(Acetyloxy)-3-nitrobenzoic acid

Product 1

HCID 120334-Hydroxy-3-nitrobenzoic acidYield 0.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-chlorotrityl chloride resin (3.00 g, 4.5 mmol) was swelled in DCM. 4-Acetoxy-3-nitro-benzoic acid (2.53 g, 11.25 mmol) was dissolved in DMF (7.5 ml) and triethylamine (1.56 ml, 11.25 ml) mixed with the drained resin. The mixture was placed on a shaker for 18 h at rt. Followed by a careful wash with DMF (3×2 min) and methanol (3×2 min). The resin was treated with a solution of 2-phanyl-ethyl amine (2M, 10 ml) in dichloromethane for 1 h at rt. and for 3 h at rt. then washed with dichloromethane (3×2 min) and dried. 36.1 mg resin was added 1% TFA in DCM 10 min filtered, added hexane and evaporated to give 4-hydroxy-3-nitro-benzoic acid (7.8 mg), which correspond to a loading of 1.18 mmol/g.

Workup

  1. washFollowed by a careful wash with DMF (3×2 min) and methanol (3×2 min)
  2. additionThe resin was treated with a solution of 2-phanyl-ethyl amine (2M, 10 ml) in dichloromethane for 1 h at rt
  3. waitand for 3 h at rt
  4. washthen washed with dichloromethane (3×2 min)
  5. customdried
  6. addition36.1 mg resin was added 1% TFA in DCM 10 min
  7. filtrationfiltered
  8. additionadded hexane
  9. customevaporated

Sources & evidence

ORD record
ord-540af2a4a39d44ccb24a4cbb390126bb
Source dataset
uspto-grants-2015_09
Patent number
US09121110B2

Reaction notes

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