4-Nitrobenzoic Acid → HCID 21552766, compound

HRID 267903Notes

Reaction equation

HRID 267903 reaction equation
[NH2:1][C:2]([CH3:14])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4].[N+:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=O)=[CH:20][CH:19]=1)([O-:17])=[O:16]>C1(C)C(C)=CC=CC=1>[CH2:7]([O:6][CH2:5][C:2]1([CH3:14])[CH2:3][O:4][C:22]([C:21]2[CH:25]=[CH:26][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=2)=[N:1]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 61084-Nitrobenzoic AcidHCID 21552765HCID 21552765, compound

Product 1

HCID 21552766HCID 21552766, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-Amino-3-benzyloxy-2-methylpropanol (13.5 grams) and 4-nitrobenzoic acid (11.7 grams) in dry xylene (100 milliliters) were heated together under reflux for 24 hours using a Dean-Stark trap for collection of the water formed during the reaction. The cooled solution was evaporated to dryness under reduced pressure and the residue was treated with ether and allowed to stand for 15 hours at 0°C. The yellow solid formed was recrystallized from ethanol to yield the desired product, melting point 65°-66°C.

Workup

  1. temperatureunder reflux for 24 hours
  2. customfor collection of the water
  3. customformed during the reaction
  4. customThe cooled solution was evaporated to dryness under reduced pressure
  5. additionthe residue was treated with ether
  6. customThe yellow solid formed
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-3fc9f4f106b044be95fcee821daaadf2
Source dataset
uspto-grants-1976_03
Patent number
US03945998

Reaction notes

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