Hydrochloric Acid → HCID 21698574, compound

HRID 379349Notes

Reaction equation

HRID 379349 reaction equation
[CH2:1]([C:3]1([CH3:12])[CH2:8][C:7]([CH3:10])([CH3:9])[CH2:6][CH:5]([NH2:11])[CH2:4]1)[CH3:2].C(N(CC)CC)C.[OH:20][C:21]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].Cl>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([C:3]1([CH3:12])[CH2:8][C:7]([CH3:10])([CH3:9])[CH2:6][CH:5]([NH:11][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[C:29]([N+:30]([O-:32])=[O:31])[C:21]=2[OH:20])[CH2:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 21698575HCID 21698575, compoundHCID 218233032-Hydroxy-3-nitrobenzoyl chloride

Product 1

HCID 21698574HCID 21698574, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred soution of 3-ethyl-3,5,5-trimethylcyclohexylamine (3.20 g, a 6:4 mixture of axial:equatorial ethyl diastereomers), triethylamine (2.13 g) and 4-dimethylaminopyridine (DMAP) (0.12 g) in dichloromethane (50 ml) was added, in a rapid dropwise manner, a solution of 2-hydroxy-3-nitrobenzoyl chloride (3.83 g) in dichloromethane (10 ml). After the addition was complete, the reaction mixture was stirred at room temperature for 12 hours, then poured into 1N HCl (250 ml). The organic layer was separated, and the aqueous layer washed with dichloromethane (50 ml). The organic phases were combined, dried (MgSO4) and the solvent evaporated to give a yellow solid (5.70 g). Recrystallization from methanol gave an analytical sample (m.p. 125-128° C.). The 13C NMR of this material showed it to be a mixture of diastereomers in an approximate ratio of 6:4.

Workup

  1. additionAfter the addition
  2. customThe organic layer was separated
  3. washthe aqueous layer washed with dichloromethane (50 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-82092f7efee646008311b965db57fe41
Source dataset
uspto-grants-2001_10
Patent number
US06297401B1

Reaction notes

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